FI112209B - trans-stereoisomeerinen sertraliinin välituote, menetelmä sen valmistamiseksi ja menetelmässä käytetty välituote - Google Patents
trans-stereoisomeerinen sertraliinin välituote, menetelmä sen valmistamiseksi ja menetelmässä käytetty välituote Download PDFInfo
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- FI112209B FI112209B FI940105A FI940105A FI112209B FI 112209 B FI112209 B FI 112209B FI 940105 A FI940105 A FI 940105A FI 940105 A FI940105 A FI 940105A FI 112209 B FI112209 B FI 112209B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C07C233/14—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/23—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
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Description
112209 trans-stereoisomeerinen sertraliinin välituote, menetelmä sen valmistamiseksi ja menetelmässä käytetty välituote Käsillä oleva keksintö kohdistuu uusiin trans-N-5 alkanoyyli-N-metyyli-4-(3,4-dikloorifenyyli)-1,2,3,4-tet-rahydro-l-naftyyliamiinianalogeihin, jotka ovat välituotteita uudessa prosessissa sertraliinin valmistamiseksi, menetelmään niiden valmistamiseksi ja menetelmässä käytettyihin välituotteisiin.
10 Täsmällisemmin käsillä oleva keksintö liittyy mai nittujen 1,4-substituoitujen tetrahydronaftyyliamiinien (1R,4S)-stereoisomeeriseen muotoon, josta N-deasyloitaessa saadaan trans-(1R,4S)-N-metyyli-4-(3,4-dikloorifenyyli)-1,2,3,4-tetrahydro-l-naftyyliamiinia. Jälkimmäinen yhdis-15 te, joka on tuotu esiin US-patenttijulkaisussa 4 556 676 sekä julkaisussa Journal of Medicinal Chemistry 27 (1984) 1508, on isomeerinen sertraliinina tai cis-(IS,4S)-N-me-tyyli-4-(3,4-dikloorifenyyli)-1,2,3,4-tetrahydro-l-naftyy-liamiinina tunnetun antidepressantin kanssa, jota puoles-20 taan on kuvattu US-patenttijulkaisussa 4 536 518 sekä julkaisussa Journal of Medicinal Chemistry 27 (1984) 1508.
: Trans- (1R, 4S) -isomeeri voidaan konvertoida cis-(lS,4S)- isomeeriksi (sertraliiniksi) tavanomaisilla menetelmillä, joista on tehty yhteenveto jäljempänä.
,···, 25 Käsillä olevan keksinnön mukaiset uudet yhdisteet • · "! on saatu käyttöön odottamattomalla havainnolla, että toi- '; ; vottua trans-isomeeriä voidaan saada stereoselektiivisesti ’· ’ suurella saannolla sopivan (1R,4S)-N-alkanoyyli-N-metyyli- 4-(3,4-dikloorifenyyli)-4-hydroksi-l,2,3,4-tetrahydro-l-; ,· 30 naftyyliamiiniprekursorin ionihydrauksella, jolloin ei- toivottu (1R, 4R)-isomeeri voidaan poistaa helposti. Koska , *, mainitussa prekursorissa on 1-(N-alkanoyyli)metyyliamino- 1 substituentti R-konfiguraatiossa, saadaan ionihydrauksella » · f trans-(1R,4S)-enantiomeeriä suurella saannolla ja korkeal- ’,,,· 35 la stereoselektiivisyydellä, ja täten vältetään optinen 2 112209 resoluutio ei-toivotun trans-(IS,4R)-enantiomeerin poistamiseksi .
Täten käsillä oleva keksintö antaa käyttöön: a) olennaisesti geometrisesti ja optisesti puhtaan 5 trans-stereoisomeerisen muodon, joka koostuu seuraavan kaavan mukaisesta trans-(1R,4S)-enantiomeeriyhdisteestä:
O
CH3N"^ri
10 rfS 15 CX
(I)
Cl jossa R1 on H tai C^-alkyyli, ja R ja S edustavat asymmet-20 risten keskusten absoluuttisia konfiguraatioita; b) prosessin olennaisesti geometrisesti ja optises-ti puhtaan kaavan (I) mukaisen yhdisteen trans-stereoiso- « I · ,···, meerisen muodon valmistamiseksi laittamalla seuraavan kaa- I · van mukainen yhdiste: 25 !!. o
II
:T: CH3y^Ri k ” CÖ
*...· s pOH
k Cx ( Il ) txi :*·. db ci • · » • * · • * 3 112209 jossa R1, R ja S ovat kuten edellä kaavan (I) kohdalla on määritelty, sopivassa liuottimessa, ionihydrausolosuhtei-siin.
Kolme tai neljä hiiliatomia sisältävät alkyyliryh-5 mät voivat olla suoraketjuisia tai haarautuneita.
Termillä "olennaisesti geometrisesti ja optisesti puhdas" tarkoitetaan sitä, että kaavan (I) mukaiset yhdisteet sisältävät vähemmän kuin 4 %, ja edullisesti vähemmän kuin 2 %, ei-toivottua cis-(1R,4R)-enantiomeeriä.
10 Edellä esitettyjen kaavan (I) ja (II) mukaisten yhdisteiden määritelmissä R1 on edullisesti H.
Käsillä olevan keksinnön mukaiset yhdisteet voidaan valmistaa seuraavasti.
Kaavan (I) mukainen yhdiste saadaan kaavan (II) 15 mukaisen yhdisteen ionihydrauksella sopivassa liuottimessa, kuten dikloorimetaanissa, käyttäen yhdistelmää, jossa on joko proottinen happo, esimerkiksi trifluorietikkahap-po, tai edullisesti Lewisin happo, esimerkiksi booritri-fluoridi, ja hydrididonori, esimerkiksi trietyylisilaani.
20 Tyypillisesti reaktio suoritetaan lämpötilassa -40 +25 °C 40 tuntiin saakka, edullisesti noin 20 tuntia. Sit- • ten kaavan (I) mukainen tuote voidaan eristää ja puhdistaa * > - · ,tavanomaisilla tekniikoilla, esimerkiksi uuttamalla ja , : sitten kromatografisella puhdistuksella ja/tai raakatuot- 25 teen kiteytyksellä jäljelle jääneen lähtömateriaalin ja pienten ei-toivotun cis-(1R,4R)-isomeerin pienten määrien ’ ; poistamiseksi. Vaihtoehtoisesti trans- ja cis-isomeerien erotukseen voidaan vaikuttaa N-alkanoyyliryhmän poistamisen jälkeen kaavan (VI) mukaisen yhdisteen saamiseksi, 30 jossa R ja S ovat kuten edellä on määritelty, seuraavassa : : kaaviossa kuvatun synteettisen sarjan mukaisesti.
* • t » 1 t » » » » » · 4 112209
Kaavio
ch3nh CH3NH
5 optinen resoluutio (MA) ^ (,IIB)
O O
10 Λ Λ CH3N ^R1 CH3N ^R1 cö-c6 l (V) (IV) 15
O O
CH3N^Ri CHaN^Ri - cO -cö spOH s jj : Cx Cl ; (II) y^ci (l) Y^ci · ' '25 Cl Cl
ch3n-h Λ rX
30 ’ s*i : : (vi) \Aa, 35 ci 5 112209
Kaavan (I) mukaisen yhdisteen N-alkanoyyliryhmä, edellä mainitun tuotteen pääisomeeri, poistetaan hydrolyy-sillä käyttäen vesipitoista epäorgaanista emästä, kuten alkalimetallihydroksidisuolaa, edullisesti kaliumhydroksi-5 dia, 10 molaarisena liuoksena vedessä. Hydrolyysi suoritetaan tyypillisesti etyleeniglykolissa reaktioalustan ref-luksilämpötilassa ajanjakson 2 tuntia - 4 päivää. Kaavan (I) mukaisen yhdisteen kohdalla, jossa R1 on H, N-alkanoyyliryhmä poistetaan edullisesti happohydrolyysillä 10 käyttäen mineraalihappoa, esimerkiksi suolahappoa, sopivassa liuottimessa, kuten 2-propanolissa, 1,4-dioksaanissa tai etyyliasetaatissa, reaktioalustan refluksilämpötilassa 2-8 tuntia. Sitten tuote (VI) eristetään ja puhdistetaan tavanomaisilla menetelmillä, esimerkiksi uuttamalla ja va-15 linnaisesti pylväskromatografoimalla pienten ei-toivottu-jen cis-(1R,4R)-isomeerin pienten määrien poistamiseksi, ja konvertoimalla se hydrokloridisuolaksi. Sitten puhdistettu vapaa amiini voidaan transformoida cis-(lS,4S)-enantiomeeriksi (sertraliiniksi), kuten jäljempänä esite-20 tyssä prosessikaaviossa on esitetty.
Kaavan (II) mukainen yhdiste, joka tarvitaan j kaavan (I) mukaisen yhdisteen valmistamiseksi, voidaan * i i saada edellä esitetyssä kaaviossa kuvatun reitin avulla, * » t jolloin R1, R ja S ovat kuten edellä on määritelty, 1 käyttäen rutiinimenetelmiä.
I I
; Alunperin amiinin (IIIA) resoluutio suoritetaan • " optisesti puhtaan R-enantiomeerin (IIIB) saamiseksi. Reso- ’ luutio suoritetaan tavanomaisella tavalla optisesti puh taan hapon, kuten sulfoni- tai karboksyylihapon, edulli-; 1 : 30 sesti (2R,3R) ( + )-viinihapon, kanssa sopivassa liuottimes- : : sa, esimerkiksi vedessä, muodostuneen amiinin (IIIA) suo lan fraktiokiteytyksellä. Sitten vapaa amiini (IIIB) va-( pautetaan käsittelemällä erotettua amiinisuolaa emäksellä, tyypillisesti natrium- tai kaliumhydroksidin vesiliuoksel-; 35 la.
t » 6 112209
Ainiini (IIIB) voidaan saada myös imiiniprekursorin asymmetrisellä pelkistyksellä, johon päästään suoraan oi-tetralonista ja metyyliamiinista alan ammattilaisten hyvin tuntemilla menetelmillä.
5 Kaavan (VI) mukainen yhdiste, jossa R1 on C1-4- alkyyli, voidaan valmistaa asyloimalla kaavan (IIIB) mukainen yhdiste joko kaavan (Ci-4-alkyyli) CO (Cl tai Br) mukaisella asyylihalidilla tai kaavan [(Ci-4-alkyyli)CO] 2O mukaisella happoanhydridillä. Kun käytetään asyylihalidia, 10 voidaan reaktio suorittaa lämpötilassa 0-25 °C, edullisesti 5-10 °C:ssa, sopivassa orgaanisessa liuottimessa, esimerkiksi dikloorimetaanissa, ja happoakseptorin, esimerkiksi trietyyliamiinin, läsnäollessa. Kun käytetään happoanhydridiä, voidaan reaktio suorittaa reaktioalustan 15 refluksilämpötilaan asti, edullisesti 100 °C:ssa, yhteensopivassa liuottimessa, esimerkiksi kaavan (Ci-4-alkyy-li)C02H mukaisessa karboksyylihapossa. Sellaisen kaavan (IV) mukaisen yhdisteen saamiseksi, jossa R1 on H, formyloidaan kaavan (IIIB) mukainen yhdiste käyttäen aset- 20 formanhydridiä, joka voidaan saada lisäämällä 98 prosenttista muurahaishappoa sekoitettuun asetanhydridiin I tyypillisesti lämpötilassa 0 - 10 °C. Sitten juuri 1 t » t valmistetun anhydridiseoksen annetaan reagoida yhdisteen t t H . (IIIB) kanssa sopivassa liuottimessa, esimerkiksi 98 25 prosenttisessa muurahaishapossa lämpötilassa 5 - 25 °C.
Kaavan (IV) mukaisen yhdisteen konversio kaavan > » (V) mukaiseksi ketoniksi bentsyylihapetusreaktion kautta I 1 V ' voidaan saavuttaa usean hapetusaineen, kuten epäorgaanisen permanganaattisuolan, ammoniumserium(IV)nitraatin, kobolt-30 ti (III) asetaatin tai 2,3-dikloori-5,6-disyano-l,4-bentso-. kinonin avulla sopivassa liuottimessa. Reaktio suoritetaan edullisesti käyttämällä 3-5 molekulaarisia kaliumperman- * · ganaattiekvivalentteja vesipitoisessa asetonissa, kun mu- kana on puskurointiainetta, kuten alkali-, maa-alkali- tai ; : 35 metallisuolaa, esimerkiksi magnesiumsulfaattia. Oksidantti ’ * »
I I
7 112209 voidaan lisätä annoksittain kontrolloidulla tavalla potentiaalisesti voimakkaan reaktion hillitsemiseksi substraat-tiliuokseen (IV) lämpötilassa 5-30 °C. Tämän lisäyksen jälkeen saatetaan tarvita reaktioseoksen lämmittäminen 5 lämpötilasta 30 °C lämpötilaan 50 °C hapettumisen saattamiseksi loppuun.
Kaavan (II) mukainen yhdiste voidaan valmistaa ste-reoselektiivisesti kaavan (V) mukaisesta yhdisteestä käyttäen 3,4-dikloorifenyylimagnesiumhalidia, edullisesti jo-10 didia, Grignardin reaktion standardiolosuhteissa. Tyypillisesti liuos, jossa on ketonista substraattia (V) yhteensopivassa liuottimessa, esimerkiksi kuivassa tolueenissa tai kuivassa tetrahydrofuraanissa, lisätään juuri valmistettuun Grignardin reagenssiliuokseen sopivassa liuotti-15 messa, kuten kuivassa dietyylieetterissä, lämpötilassa 5 -25 °C vedettömissä olosuhteissa. Reaktion annetaan edetä lämpötilassa 20 - 25 °C 4 - 24 tuntia ja seosta voidaan lämmittää refluksissa 1 tuntiin saakka tarpeen mukaan, jolloin yhdiste (V) konvertoituu paremmin yhdisteeksi 20 (II). Pienet (1R,4R)-alkoholimäärät voidaan poistaa pyl- väskromatografisesti ja/tai kiteyttämällä.
: ’. Trans-(1R, 4S)-amiini (VI) voidaan konvertoida sert- . ·, raliiniksi seuraavalla prosessilla.
* · * t I · • · » ’ ► 112209 8 H CH-, N R r ^sY (vi) 5 / ci 10 / .CH,
N
15 ^ (VII)
Vei
H CH, H ,CHS
V 3 N
: r= sl
: ; 25 QO CO
• (vi) I li l il sertraliini ; : γχι ci ci : 30 , t 9 112209
Prosessiin kuuluu trans-enantiomeerin (VI) kontrolloitu hapetus, jotta saadaan imiiniä (VII), joka myöhemmin pelkistetään esimerkiksi katalyyttisellä hydrauk-sella käyttäen 10 prosenttista palladioitua hiiltä kata-5 lyyttinä, kuten US-patenttijulkaisussa 4 536 518 on kuvattu, sertraliiniseoksen (suhde noin 7:3) saamiseksi ja ottamalla talteen yhdiste (VI); jälkimmäinen voidaan erottaa sertraliinista tavanomaisilla tavoilla ja sitä voidaan kierrättää uusien sertraliiniannosten saamiseksi.
10 Vaihtoehtoisesti voidaan käyttää nikkelipohjaisia kata lyyttejä hydrausvaiheessa sertraliinin ja yhdisteen (VI) seoksen (suhde noin 8:1) saamiseksi.
Alla kuvatussa vaihtoehtoisessa optimointiproses-sissa voidaan cis-(1R,4R)-enantiomeeriä (VIII), joka yh-15 dessä yhdisteen (VI) kanssa on ei-toivottu sivutuote prosesseissa, joissa sertraliinia tuotetaan kaikkien neljän stereoisomeerin seoksen resoluutiolla, kierrättää myös sertraliiniksi imiiniyhdisteen (VII) kautta. Ensin kuitenkin yhdiste (VIII) isomeroidaan emäskäsittelyllä yhdisteen 20 (VIII) ja trans-(1R,4S)-enantiomeerin (VI) seokseksi (suh de noin 2:1) ja tämän jälkeen jälkimmäinen erotetaan ja : konvertoidaan imiiniksi (VII), kuten edellä esitetyssä • · · » .···. ensimmäisessä uudelleenkierrätysprosessissa. Jäljelle jää- nyt cis-(1R,4R)-enantiomeeri (VIII) voidaan käsitellä uu- • · ... 25 delleen tarpeen mukaan tällä tasapainoprosessilla.
• · • i · • 1 » ♦ • · 1 • 1 · • · » • t · • · • » · a · • · · • · 1 • · • « a a » i
• I
• I
i t i • a 10 112209 H .CM3 R = V"’ H. .CHj = φ - Φ . Cö Φ Φ φ
(VIII) \ / α CI
(VIII) (VI) 10 ^ .CH, Ν (VII) α 20
Vaihtoehtoisesti tähän liittyvässä prosessissa ei- t toivottu cis-(1R,4R)-enantiomeeri (VIII) voidaan hapettaa α-tetraloniksi (IX), joka puolestaan voidaan isomeroida 25 tunnetun, raseemisen, US-patenttijulkaisussa 4 536 518 sekä julkaisussa Journal of Medicinal Chemistry 27 (1984) - · * 1508 kuvatun 4-(3,4-dikloorifenyyli)-a-tetralonin (X) saa- * miseksi. Tämän jälkeen yhdiste (X) transformoidaan sertra- liiniksi raseemisen imiinin (XI) kautta, edullisesti yh-·’ 30 disteen (XI) katalyyttisellä hydrauksella käyttämällä pal ladium- tai nikkelikatalyyttiä, kuten edellä on mainittu, • ja erottamalla tämän jälkeen cis-rasemaatti ja suoritta malla sitten sen resoluutio, kuten US-patenttijulkaisussa 4 536 518 on kuvattu. Tämä prosessi on kuvattu seuraavalla :.,,ί 35 sivulla.
11 112209 Η· -CH> n
N J O
Φ — Φ _oö φ Φ ςκ et Cl C1 (VIII) (IX) / (χ)
i° X
,ch3 X
N / (XI) 15 Cl a ^_A, /XCH- H-N'CH> »„-“> H. .CH, ^ SJF /SR1 eV rn
: Op Φ Φ OQ
;; 25 9^ τα τ» Ψα (VI) sertraliini (VIII)
:V: V-Y-' V_^ ,_J
Y γ iv 30 • · » • · · 1 1 i 112209 12 Käsillä olevaa keksintöä kuvataan nyt yksityiskohtaisemmin seuraavien esimerkkien avulla. Yhdisteiden puhtaus tarkastettiin ohutlevykromatografisesti (TLC) käyttämällä Merckin Kieselgel 60 F254 -levyjä. Rutiininomaiset 5 1H-ydinmagneettiresonanssispektrit (nmr) mitattiin käyttäen Nicolet QE-300 -spektrometriä ja 13C-nmr-spektrit mitattiin käyttäen Bruker 250 -spektrometriä; ne olivat kaikissa tapauksissa yhtäpitävät ehdotettujen rakenteiden kanssa. Ytimen Overhauser-vaikutuskokeet (nOe) suoritet- 10 tiin käyttäen Bruker 250 -spektrometriä.
Esimerkki 1 (R)(-)-N-metyyli-1,2,3,4-tetrahydro-l-naftyyli- amiini
Liuosta, jossa oli (2R,3R)(+)-viinihappoa 15 (160,3 g) vedessä (500 ml), käsiteltiin N-metyyli-1,2,3,4- tetrahydro-l-naftyyliamiinilla (172,2 g). Tuloksena saatu liuos jäähdytettiin lämpötilasta 33 °C huoneenlämpöön, siemennettiin ja sitä sekoitettiin 16 tuntia. Lietettä pidettiin kylmässä 4 tuntia, se suodatettiin ja kiinteä 20 aines pestiin vedellä (3 x 50 ml). Raaka suola (196,2 g) jakokiteytettiin uudelleen vedestä, jolloin saatiin otsi-• ·’; kon mukaisen yhdisteen puhdasta ( + )-viinahapposuolaa (42 g, 25,3 % perustuen saatavissa olevaan enantiomeeriin) valkoisina kiteinä, sp. 107 - 109 °C, [a]D +12,3° (c = 4,2, I · ...t 25 vesi). Löydetty: C 54,85, H 7,06, N 4,22. Yhdiste C15H21NO6 "] . H2O vaatii C 54,70, H 7,04, N 4,25 %.
» · "I Suola (38,9 g) liuotettiin veteen (150 ml) samalla i · * lämmittäen 40 °C:seen ja sitten liuos tehtiin emäksiseksi lisäämällä 5 N natriumhydroksidin vesiliuosta (100 ml).
30 Jäähtynyttä seosta uutettiin dikloorimetaanilla (2 x : 150 ml). Sen jälkeen kun uutteet oli haihdutettu tyhjössä, •t saatiin otsikon mukaista yhdistettä värittömänä öljynä (19,1 g, 97,2 % suolasta), [cx]d -10,3° (c = 5, EtOH) .
C (+)-α-metoksi-a-(trifluorimetyyli)fenyyliasetyylijohdan- ! 35 naisen 1H-nmr-määritys käyttäen Mosherin menetelmää »
< I
13 112209 (J. Org. Chem. 34 (1969) 2543) osoitti, että otsikon mu kainen yhdiste oli (R)- ja (S)-enantiomeerien 95,5:4,5 seos.
Esimerkki 2 5 (R)(+)-N-(1,2,3,4-tetrahydro-l-naftyyli)-N-metyy- liformamidi
Asetanhydridi (54,1 g) jäähdytettiin 0°C:seen ja sitä sekoitettiin samalla, kun 98 % muurahaishappoa (33,1 g) lisättiin 30 minuutin aikana, ja lämpötila pidet-10 tiin alle 5 °C:ssa. Liuos lämmitettiin 50 °C:seen, sitä pidettiin tässä lämpötilassa 15 minuuttia ja sitten se jäähdytettiin 5 °C:seen. Tuloksena saatu aset-formanhydri-diliuos lisättiin 5 minuutin aikana sekoitettuun, jäähdytettyyn liuokseen, jossa oli (R)(-)-N-metyyli-1,2,3,4-tet-15 rahydro-l-naftyyliamiinia (19,08 g) 98 prosenttisessa muurahaishapossa (19,08 ml), ja lämpötila pidettiin alle 10 °C:ssa. Reaktioliuos lämmitettiin huoneenlämpöiseksi, sitä sekoitettiin 1 tunti, se kaadettiin jää-vesiseokseen (200 g) ja sitä sekoitettiin 30 minuuttia. Seos tehtiin 20 emäksiseksi arvoon pH 9 10 N natriumhydroksidin vesiliuoksella (noin 230 ml) ja sitä uutettiin dikloorimetaanilla . (3 x 200 ml). Yhdistetyt uutteet takaisinpestiin 1 N suo- lahappoliuoksella (100 ml), sitten vedellä (100 ml) ja ; haihdutettiin tyhjössä, jolloin saatiin otsikon mukaista » 25 yhdistettä (21,63 g, 96,6 %) kiinteänä aineena, s.p. 53 -55 °C; Rf 0,80 (silika, kloroformi/metanoli 95:5).
y·1 Näyte tuotetta (1,5 g) kiteytettiin seoksesta, t i · V ’ jossa oli etyyliasetaattia (1,5 ml) ja heksaania (15 ml), jolloin saatiin otsikon mukaisen yhdisteen puhdistettua • i « | 30 näytettä (0,92 g, saanto 61,3 %) valkoisina kiteinä, sp.
55 - 56 °C, [a]D +19,4° (c = 0,5, EtOH) . Kiraali HPLC mää- (Λ( ritys asetyloidussa β-syklodekstriinipylväässä osoitti * i · tämän materiaalin sisältävän vähemmän kuin 1 % (S)-enan-tiomeeriä. Löydetty: C 76, 04, H 7,94, N 7,43. Yhdiste 35 C12H15NO vaatii C 76,16, H 7,98, N 7,40 %.
14 112209 1H-nmr (300 MHz, CDC13): δ = 1,80 - 2,13 (m, 4H), 2,70 ja 2,73 (2 NMe rotameeri singletit, 3H), 2,78 - 2,93 (m, 2H), 4,73 - 4,81 ja 5,71 - 5,79 (2 rotameeri multi-pletit, 1H), 7,02 - 7,25 (m, 4H), 8,30 ja 8,34 (2 formyyli 5 CH rotameeri singletit, 1H) ppm.
Esimerkki 3 (R)(+)-N-(1,2,3,4-tetrahydro-4-keto-l-naftyyli)-N- metyy1iformamidi Jäähdytettyyn liuokseen, jossa oli (R)(+)-N-(1,2,-10 3,4-tetrahydro-l-naftyyli)-N-metyyliformamidia (19,1 g) asetonissa (430 ml), lisättiin magnesiumsulfaattiheptahyd-raattia (57 g), vettä (143 ml) ja sitten annoksittain tunnin aikana kaliumpermanganaattia (76 g). Seosta sekoitettiin 5,5 tuntia jäähdyttävässä vesihauteessa reaktiolämpö-15 tilan pitämiseksi alle 34 °C:ssa, seos suodatettiin ja kakku pestiin asetonilla (2 x 100 ml). Suodos ja pesuvedet yhdistettiin ja niitä käsiteltiin 10 % natriummetabisul-faatin vesiliuoksella (140 ml), sitten seos uudelleensuo-datettiin ja sitä uutettiin dikloorimetaanilla (400 ml ja 20 sitten 200 ml). Yhdistetyt uutteet haihdutettiin tyhjössä öljyksi (14,7 g), joka kromatografoitiin silikalla (274 g) ; eluoiden dikloorimetaani/metanoli seoksella (98:2), ja ’·· ’ näin saatiin tuotetta öljynä (8,2 g, 40 %); Rf 0,18 (sili-
• I
. ka, etyyliasetaatti) ja 0,58 (silika, kloroformi/metanoli 1 2 3 4 5 6 7 8 9 10 11 95:5).
2
• I
3 '· Tuotenäytettä (1,1 g) trituroitiin dietyylieette- 4 rillä (20 ml) kiteytyksen aikaansaamiseksi ja näin saatiin , ’ puhdistettua otsikon mukaista tuotetta (0,72 g), s.p. 92 - 5
93 °C; [a]D +54,9° (c = 0,5, EtOH). Löydetty: C 70,68, H
6
6,41, N 6,86. Yhdiste C12H13N02 vaatii C 70,92, H 6,45, N
7 6,64 %.
8 Λ 1H-nmr (300 MHz, CDC13): δ = 2,17 - 2,56 (m, 2H), 9 2,68 - 2,99 (m, 2H), 2,79 ja 2,83 (2 NMe rotameerisingle- 10 tit, 3H), 4,96 - 5,04 ja 5,92 - 6,01 (2 rotameerikvarte- 11 tit, 1H), 7,10 - 7,24 (q, 1H), 7,40 - 7,53 (m, 1H), 7,55 -
' I
15 112209 7,68 (m, 1H), 8,07 - 8,16 (t, 1H), 8,38 ja 8,40 (2 formyy-li CH rotameerisingletit, 1H) ppm.
Esimerkki 4 (1R,4S) (-)-N-[4-(3,4-dikloorifenyyli)-1,2,3,4- 5 tetrahydro-4-hydroksi-l-naftyyli]-N-metyyliform- amidi
Magnesiumlastuja (0,89 g) ja jodikidettä sekoitettiin kuivassa dietyylieetterissä (25 ml) , kun liuosta, jossa oli 1,2-dikloori-4-jodibentseeniä (10,07 g) kuivassa 10 dietyylieetterissä (25 ml), lisättiin 20 minuutin aikana.
Sen jälkeen kun eksoterminen reaktio oli mennyt loppuun, seosta lämmitettiin refluksissa vielä 25 minuuttia magne-siummetallin kulutuksen viemiseksi loppuun. Sitten seos jäähdytettiin 5 °C:seen, peitettiin typpikaasulla ja 15 liuosta, jossa oli (R) (+)-N-(1,2,3,4-tetrahydro-4-keto-l-naftyyli)-N-metyyliformamidia (5 g) kuivassa tolueenissa (100 ml), lisättiin 15 minuutin aikana. Sen jälkeen, kun näin saatua seosta oli sekoitettu 20 tuntia, se kaadettiin 10 prosenttiseen ammoniumkloridin vesiliuokseen (200 ml) .
20 Faasit erotettiin, vesifaasi pestiin tolueenilla (25 ml) ja yhdistetyt orgaaniset kerrokset haihdutettiin tyhjössä, jolloin saatiin (1R,4 S)— ja (1R,4R)-isomeerien seosta j (suhde 87:13 vastaavasti nmr-spektroskopiatekniikoilla) tummana öljynä (10,17 g), joka kromatografoitiin silikalla 25 (320 g). Sen jälkeen, kun sitä oli eluoitu heksaani-etyy- liasetaattiseoksilla (1:1 - 1:4), saatiin otsikon mukaista ; yhdistettä vaahtona (3,94 g, 45,7 %) , Rf 0,34 (silika, , · etyyliasetaatti) ja 0,50 (silika, kloroformi/metanoli 95:5), joka oli riittävän puhdasta käytettäväksi seuraa-30 vassa vaiheessa.
*; Näyte tuotetta (0,92 g) puhdistettiin hitaalla ki- i i , , teytyksellä di-2-propyylieetteristä ja näin saatiin otsi-
I ' I
kon mukaista yhdistettä (0,46 g, saanto 50 %) valkoisina kiteinä, sp. 123 - 125 °C, [a]D -31,6° (c = 0,5, EtOH) .
» > i » t « 16 112209 / Löydetty: C 61,79, H 5,07, N 3,90. Yhdiste C18H17CI2NO2 vaatii C 61,72, H 4,89, N 4,00 %.
1H-nmr (300 MHz, CDC13) : δ = 1,60 - 2,01 (m, 2H) , 2,12 - 2,37 (m, 2H) , 2,38 (s, 1H) , 2,69 ja 2,73 (2 NMe 5 rotameerisingletit, 3H), 4,78 - 4,86 ja 5,75 - 5,83 (2 ro-tameerikvartetit, 1H) , 6, 89 - 7,04 (m, 1H) , 7,05 - 7,42 (m, 6H) , 8,25 ja 8,30 (2 formyyli CH rotameerisingletit, 1H) ppm.
Esimerkki 5 10 Trans-(1R,4S)(+)-N-[4-(3,4-dikloorifenyyli)-1,2,- 3,4-tetrahydro-l-naf tyyli] -N-metyyliformamidi
Liuokseen, jossa oli (1R,4S)(+)-N-[4-(3,4-dikloo-rifenyyli)-1,2,3,4-tetrahydro-4-hydroksi-l-naftyyli]-N-metyyliformamidia (0,175 g) dikloorimetaanissa (10 ml), 15 lisättiin trietyylisilaania (0,13 g) dikloorimetaanissa (1 ml). Tuloksena saatu liuos jäähdytettiin -40 °C:seen ja siihen lisättiin samalla sekoittaen booritrifluoridia (0,08 g) dikloorimetaanissa (6,5 ml) 30 minuutin aikana.
Liuoksen annettiin lämmetä huoneenlämpöiseksi 90 minuutin 20 aikana ja sitten sitä käsiteltiin vielä trietyylisilaanil-la (0,13 g) dikloorimetaanissa (1 ml) ja sitten vielä boo-; ritrifluoridilla (0,54 g) dikloorimetaanissa (43,5 g). Sen , jälkeen, kun liuosta oli sekoitettu yön yli huoneenlämmös- , : sä, tehtiin vielä kolmas trietyylisilaanilisäys (0,13 g) 25 ja liuosta kaasutettiin booritrifluoridilla noin 1 minuut- • · ti. Tuloksena saatu liuos pestiin 2 M natriumkarbonaatti-vesiliuoksella (22 ml) ja sitten kyllästetyllä suolavedellä (25 ml) ja vesifaasit yhdistettiin ja takaisinpestiin dietyylieetterillä (2 x 25 ml). Yhdistetyt orgaaniset uut-30 teet kuivattiin magnesiumsulfaatilla ja haihdutettiin tyh-/> jössä, jolloin saatiin öljyä (0,17 g), joka perkoloitiin silikageelipylvään (16 g) läpi eluoiden 1:1 etyyliasetaat-! ti-heksaanilla jäljelle jääneen pienen materiaalimäärän poistamiseksi. Tarpeelliset fraktiot haihdutettiin tyhjös-' 35 sä ja näin saatiin raakatuotetta öljynä (154 mg, 92 %) .
> f * 17 112209 Tämän materiaalin 1H-nmr-määritys osoitti sen olevan halutun (1R, 4S)-trans-isomeerin (δ = 4,04 - 4,14 ppm, m, H4-protonille) ja (1R,4R)-cis-isomeerin (δ = 4,18 - 4,27 ppm, m, H4-protonille) 86:14-seos.
5 Trans- ja cis-isomeerien erotus saavutetaan tehok kaimmin formyyliryhmän poistamisen jälkeen. Kuitenkin raa-katuotenäytteen kiteytys 1:3 dikloorimetaani-heksaanista antoi käyttöön otsikon mukaisen yhdisteen referenssinäy-tettä valkoisina kiteinä, s.p. 110 - 112 °C, Rf 0,62 (si-10 lika, kloroformi/metanoli 95:5); [cx]d +100,8° (c = 1,03, EtOH). Löydetty: C 64,66, H 5,37, N 4,12. Yhdiste
Ci8Hi7C12NO vaatii C 64,67, H 5,13, N 4,19 %.
1H-nmr (300 MHz, CDC13) : δ = 1,88 - 2,18 (m, 3H) , 2,21 - 2,37 (m, 1H), 2,73 ja 2,78 (2 NMe rotameerisingle-15 tit, 3H) , 4,04 - 4,14 (m, 1H) , 4,90 - 4,98 ja 5,84 - 5,96 (2 rotameerimultipletit, 1H) , 6,77 - 6,85 (t, 1H) , 6,91 -7,03 (m, 1H) , 7,05 - 7,34 (m, 4H) , 7,36 - 7,47 (m, 1H) , 8,34 ja 8,38 (2 formyyli CH rotameerisingletit, 1H) ppm. Esimerkki 6 20 Trans-(1R,4S)(+)-N-metyyli-4-(3,4-dikloorifenyy- li)-1,2,3,4-tetrahydro-l-naftyyliamiinihydro-kloridi
Liuosta, jossa oli trans-(1R,4 S) ( + )-N-[4-(3,4-di-, ; klooritenyyli)-1,2,3,4-tetrahydro-l-naftyyli]-N-metyyli- 25 formamidia (0,15 g 86:14 trans-cis-seosta esimerkistä 5) '; 2-propanolissa (1,5 ml), käsiteltiin konsentroidulla vesi- ' ·' pitoisella suolahapolla (0,45 ml) ja tätä seosta refluk- ’ * soitiin 12,5 tuntia. Liuosta pidettiin kylmässä yön yli, ja sitten tuloksena saatua seosta granuloitiin 0 °C:ssa 30 useita tunteja. Suodatuksen jälkeen saatiin tuotetta : (0,119 g, 71,4 %) valkoisina kiteinä, s.p. 253 - 255 °C; • ^ Rf 0,09 (silika; kloroformi/metanoli 90:10); [ö]d +41,4° f’ (c = 1, MeOH).
·* N-metyyli-1,2,3,4-tetrahydro-l-naftyyliamiinia 35 (yhdiste IIIA) saadaan julkaisussa Coll. Czech. Chem.
Commun. 38 (1973) 1159 kuvatun menetelmän mukaisesti.
f 1 4
Claims (10)
1. Menetelmä kaavan (I) mukaisen yhdisteen olen-5 naisesti geometrisesti ja optisesti puhtaan trans-stereo-isomeerisen muodon valmistamiseksi, O « CHoN'^^R1 10 r^tS (.) T^CI Cl jossa R1 on H tai Ci-4-alkyyli, ja R ja S edustavat 20 asymmetristen keskusten absoluuttisia konfiguraatioita, tunnettu siitä, että ionihydrataan yhdiste, jolla h on kaava t
25 Jk ch3n^r1 :* rJ^ CQ 30. i OH ? ÖL !:; di) Cl ; * 0 35 112209 jossa R1, R ja S ovat kuten edellä kaavan (I) kohdalla on määritelty.
2. Patenttivaatimuksen 1 mukainen menetelmä, tunnettu siitä, että ionihydraus saadaan aikaan 5 käyttäen Lewisin hapon ja hydrididonorin yhdistelmää.
3. Patenttivaatimuksen 1 mukainen menetelmä, tunnettu siitä, että ionihydraus saadaan aikaan käyttäen proottisen hapon ja hydrididonorin yhdistelmää.
4. Patenttivaatimuksen 2 mukainen menetelmä, 10 tunnettu siitä, että Lewisin happo on boori- trifluoridi.
5 A CH3N^r1 cö sT^OH 10 ΓΊ (il) γ'χι ci 15 jossa R1 on H tai C-^-alkyyli, ja R ja S edustavat asymmetristen keskusten absoluuttisia konfiguraatioita.
5. Patenttivaatimuksen 3 mukainen menetelmä, tunnettu siitä, että proottinen happo on trifluorietikkahappo.
6. Minkä tahansa patenttivaatimuksen 2-5 mukai nen menetelmä, tunnettu siitä, että hydrididonori on trietyylisilaani.
7. Minkä tahansa patenttivaatimuksen 1-6 mukainen menetelmä, tunnettu siitä, että R1 on H.
8. Kaavan (I) mukaisen yhdisteen olennaisesti geo- metrisesti ja optisesti puhdas trans-stereoisomeerinen muoto, 0
25 CH3y^R1 30 (1) v.: Cl ‘1* jossa R1 on H tai Ci-4-alkyyli, ja R ja S edustavat :,(t: 35 asymmetristen keskusten absoluuttisia konfiguraatioita. * · 112209
9. Kaavan (II) mukainen yhdiste O
10. Patenttivaatimuksen 8 tai 9 mukainen yhdiste tunnettu siitä, että R1 on H. « > · » » 112209
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GB919114948A GB9114948D0 (en) | 1991-07-11 | 1991-07-11 | Process for preparing sertraline intermediates |
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EP9201496 | 1992-07-03 | ||
PCT/EP1992/001496 WO1993001161A1 (en) | 1991-07-11 | 1992-07-03 | Process for preparing sertraline intermediates |
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US4536518A (en) * | 1979-11-01 | 1985-08-20 | Pfizer Inc. | Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
US4556676A (en) * | 1979-11-01 | 1985-12-03 | Pfizer Inc. | Antidepressant derivatives of trans-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
-
1991
- 1991-07-11 GB GB919114948A patent/GB9114948D0/en active Pending
-
1992
- 1992-07-03 US US08/178,240 patent/US5442116A/en not_active Expired - Fee Related
- 1992-07-03 JP JP5501952A patent/JP2563754B2/ja not_active Expired - Fee Related
- 1992-07-03 AT AT92914659T patent/ATE132848T1/de not_active IP Right Cessation
- 1992-07-03 EP EP92914659A patent/EP0595851B1/en not_active Expired - Lifetime
- 1992-07-03 CA CA002109818A patent/CA2109818C/en not_active Expired - Fee Related
- 1992-07-03 ES ES92914659T patent/ES2082481T3/es not_active Expired - Lifetime
- 1992-07-03 WO PCT/EP1992/001496 patent/WO1993001161A1/en active IP Right Grant
- 1992-07-03 DK DK92914659.5T patent/DK0595851T3/da active
- 1992-07-03 DE DE69207601T patent/DE69207601T2/de not_active Expired - Fee Related
- 1992-07-09 PT PT100673A patent/PT100673B/pt not_active IP Right Cessation
- 1992-07-10 IE IE922249A patent/IE71029B1/en not_active IP Right Cessation
-
1994
- 1994-01-10 FI FI940105A patent/FI112209B/fi not_active IP Right Cessation
-
1996
- 1996-02-28 GR GR960400546T patent/GR3019122T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
ATE132848T1 (de) | 1996-01-15 |
ES2082481T3 (es) | 1996-03-16 |
GR3019122T3 (fi) | 1996-05-31 |
DE69207601T2 (de) | 1996-05-23 |
JP2563754B2 (ja) | 1996-12-18 |
PT100673B (pt) | 1999-07-30 |
CA2109818C (en) | 2003-01-21 |
IE922249A1 (en) | 1993-01-13 |
CA2109818A1 (en) | 1993-01-12 |
FI940105A (fi) | 1994-01-10 |
US5442116A (en) | 1995-08-15 |
IE71029B1 (en) | 1997-01-15 |
EP0595851B1 (en) | 1996-01-10 |
EP0595851A1 (en) | 1994-05-11 |
FI940105A0 (fi) | 1994-01-10 |
DK0595851T3 (da) | 1996-02-12 |
WO1993001161A1 (en) | 1993-01-21 |
JPH06509079A (ja) | 1994-10-13 |
PT100673A (pt) | 1993-09-30 |
GB9114948D0 (en) | 1991-08-28 |
DE69207601D1 (de) | 1996-02-22 |
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