GB1352637A - Process for the manufacture of optically active bicycloalkane derivatives - Google Patents

Process for the manufacture of optically active bicycloalkane derivatives

Info

Publication number
GB1352637A
GB1352637A GB2406071*A GB2406071A GB1352637A GB 1352637 A GB1352637 A GB 1352637A GB 2406071 A GB2406071 A GB 2406071A GB 1352637 A GB1352637 A GB 1352637A
Authority
GB
United Kingdom
Prior art keywords
chloro
indanedione
dihydro
phenylenedioxy
ortho
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2406071*A
Inventor
U Eder
R Wiechert
G Sauer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Pharma AG
Original Assignee
Schering AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering AG filed Critical Schering AG
Publication of GB1352637A publication Critical patent/GB1352637A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
    • C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
    • C07C49/623—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
    • C07C49/637—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing ten carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/613—Unsaturated compounds containing a keto groups being part of a ring polycyclic
    • C07C49/617—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system
    • C07C49/623—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
    • C07C49/633—Unsaturated compounds containing a keto groups being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing eight or nine carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/693—Unsaturated compounds containing a keto groups being part of a ring containing halogen polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1352637 Indane and naphthalene derivatives SCHERING AG 19 April 1971 [20 March 1970 9 March 1971] 24060/71 Heading C2C Optically active compounds of the Formula I in which n represents 1 or 2, R 1 represents an aliphatic hydrocarbon group containing up to 4 carbon atoms, m represents 0, 1 or 2 and R 2 represents a hydrogen atom, a free or esterified carboxyl group, a free, etherified or esterified α- hydroxyalkyl group containing 2 to 4 carbon atoms, a haloalkenyl group containing 2 to 5 carbon atoms, a ketalized 1-oxoalkyl group containing 2 to 4 carbon atoms, an unsubstituted phenyl group or a phenyl group substituted by one or more substituents selected from halogen atoms and acylamino, alkyl, free amino, alkylamino, hydroxyl, alkoxy and acyloxy groups, are prepared by cyclizing a cycloalkane- 1,3-dione of the Formula II in a polar solvent in the presence of an optically active amino compound and of H<SP>+</SP> ions, the optically active amino being used in an amount of at least 0À1 mole per mole of the cycloalkane- 1,3-dione. Examples of optically active amino compounds are optical antipodes of aminoacids such as proline, alanine and phenylalanine, and α-arylaminoalkanes such as α- phenylethylamine and α-(1-naphthyl)-ethylamine. The solvent may be, for example, a carboxylic acid, dimethylformamide or acetonitrile. H<SP>+</SP> ions may be supplied by dilute mineral acids such as HCl or perchloric acid. The compound I formed may in the D- or L- form depending on which antipode of the optically active amino compound is present in the batch. Some of the products are claimed per se, namely (+) - 8a - n - butyl - 3,4,8,8a - tetrahydro - 1,6(2H,7H) - naphthalenedione, (+)- 7,7a - dihydro - 7a - ethyl - 1,5(6H) - indanedione, (+ ) - 7,7a - dihydro - 4,7a - dimethyl - 1, 5(6H) - indanedione, (+) - 7,7a - dihydro - 7amethyl - 4 - [2<SP>1</SP> - (meta - methoxyphenyl)- ethyl] - 1,5(6H) - indanedione, (+ ) - 7,7a - dihydro - 7a - methyl - 4 - [3<SP>1</SP>,3<SP>1</SP> - (ortho - phenylenedioxy) - butyl] - 1,5(6H) - indanedione and (+) - 7,7a - dihydro - 7a - methyl - 4 - (3<SP>1</SP>- chloro-2<SP>1</SP>-butenyl)-1,5(6H)-indanedione. Starting materials and intermediates.-7,7a- Dihydro - 7a - methyl - 4 - [3<SP>1</SP>,3<SP>1</SP> - (orthophenylenedioxy) - butyl] - 1,5(6H)-indanedione is prepared via 5,5 - (orthophenylenedioxy) - hexanoic acid ethyl ester, 5,5 - (ortho - phenylenedioxy) - hexan- 1 - ol, 5,5 - (ortho - phenylenedioxy) - hexanal, 7, 7 - (ortho - phenylenedioxy) - 1 - octen - 3 - ol, 7,7- (ortho - phenylenedioxy) - 1 - octen - 3 - one and 2 - methyl - [3<SP>1</SP>- oxo - 7<SP>1</SP>,7<SP>1</SP> - (ortho - phenylenedioxy) - octyl] - cyclopentane - 1,3 - dione. 7,7a- Dihydro - 7a - methyl - 4 - (3<SP>1</SP> - chloro - 2<SP>1</SP> - butenyl) - 1,5(6H) - indanedione is prepared via 4 - chloro - 3 - pentene - 1,1 - dicarboxylic acid diethyl ester, 5-chloro-4-hexenic acid, 5-chloro-4- hexen - 1 - ol, 5 - chloro - 4 - hexenal, 7 - chloro- 1,6 - octadien - 3 - ol, 7 - chloro - 1,6 - octadien- 3 - one and 2 - methyl - 2 - (3<SP>1</SP> - oxo - 71 - chloro- 6<SP>1</SP>-octenyl)-cyclopentane-1,3-dione.
GB2406071*A 1970-03-20 1971-04-19 Process for the manufacture of optically active bicycloalkane derivatives Expired GB1352637A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE19702014757 DE2014757A1 (en) 1970-03-20 1970-03-20 Process for the preparation of optically active bicycloalkane derivatives

Publications (1)

Publication Number Publication Date
GB1352637A true GB1352637A (en) 1974-05-08

Family

ID=5766475

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2406071*A Expired GB1352637A (en) 1970-03-20 1971-04-19 Process for the manufacture of optically active bicycloalkane derivatives

Country Status (19)

Country Link
JP (1) JPS546550B1 (en)
AT (1) AT305971B (en)
BE (1) BE764509A (en)
CH (1) CH549548A (en)
CS (1) CS155969B2 (en)
DE (1) DE2014757A1 (en)
DK (1) DK142312C (en)
ES (1) ES389292A1 (en)
FR (1) FR2084893A5 (en)
GB (1) GB1352637A (en)
IE (1) IE35258B1 (en)
IL (1) IL36432A (en)
IT (1) IT1047887B (en)
NL (1) NL7103841A (en)
PH (1) PH9907A (en)
PL (1) PL83133B1 (en)
SE (1) SE374101B (en)
YU (2) YU35432B (en)
ZA (1) ZA711253B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0045219A1 (en) * 1980-07-30 1982-02-03 Beecham Group Plc Reduced naphthalenes, their preparation and use

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6042775B2 (en) * 1977-10-11 1985-09-25 三菱油化株式会社 1,7-octadien-3-one and its manufacturing method

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0045219A1 (en) * 1980-07-30 1982-02-03 Beecham Group Plc Reduced naphthalenes, their preparation and use

Also Published As

Publication number Publication date
PL83133B1 (en) 1975-12-31
SU373936A3 (en) 1973-03-12
ZA711253B (en) 1971-11-24
IL36432A (en) 1975-10-15
JPS546550B1 (en) 1979-03-29
YU35432B (en) 1981-02-28
DE2014757A1 (en) 1971-10-07
AT305971B (en) 1973-03-26
NL7103841A (en) 1971-09-22
IE35258L (en) 1971-09-20
DK142312C (en) 1981-03-23
BE764509A (en) 1971-09-20
IL36432A0 (en) 1971-05-26
DK142312B (en) 1980-10-13
PH9907A (en) 1976-06-06
CS155969B2 (en) 1974-06-24
FR2084893A5 (en) 1971-12-17
YU57171A (en) 1980-09-25
CH549548A (en) 1974-05-31
SE374101B (en) 1975-02-24
ES389292A1 (en) 1973-06-16
IE35258B1 (en) 1975-12-24
IT1047887B (en) 1980-10-20

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee