GB1439542A - Derivatives of norbornene - Google Patents

Derivatives of norbornene

Info

Publication number
GB1439542A
GB1439542A GB4052973A GB4052973A GB1439542A GB 1439542 A GB1439542 A GB 1439542A GB 4052973 A GB4052973 A GB 4052973A GB 4052973 A GB4052973 A GB 4052973A GB 1439542 A GB1439542 A GB 1439542A
Authority
GB
United Kingdom
Prior art keywords
endo
methyl
dimethyl
norbornen
exo
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
GB4052973A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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 F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1439542A publication Critical patent/GB1439542A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1439542 Derivatives of norbornene compounds F HOFFMAN-LA ROCHE & CO AG 28 Aug 1973 [28 Aug 1972] 40529/73 Heading C2C The invention comprises a racemic or optically active compound of formula where R<SP>1</SP> represent a hydrogen atom or the acid residue of an aromatic or aliphatic dicarboxylic acid, an optically active aliphatic or araliphatic monocarboxylic acid, an optically active sulphonic acid or an optically active carbamic acid. The invention also comprises the tetrahydropyranyl ethers of above compound which are represented by formula The invention also comprises a compound of formula where R<SP>4</SP> represents a sulphonyloxy group derived from an organic sulphonic acid, or a Cl, Br, or I 2 atom and R 2 is an acid residue of an aliphatic dicarboxylic acid, and optically active aliphatic or araliphatic monocarboxylic acid, an optically active sulphonic acid or an optically active carbamic acid. This compound may be obtained by reductively opening the anhydride group of 5,6-dimethyl-bicyclo[2,2,1] hept-5-en-2-endo-3-endo-dicarboxylic acid anhydride and, if desired, esterifying a hydroxy group of the thus obtained 5,6-dimethylbicyclo [2,2,1]hept - 5 - en - 2 - endo - 3 - endo - dimethanol with a compound yielding an acid residue R<SP>1</SP> and, also if desired, separating a diastereomer pair thereby obtained or resolving a recemate thereby obtained. The invention also comprises two further processes in which starting with the compound according to the invention there are obtained, through a long series of reactions, compounds of formulae In the preparation of compounds XV and XVa and the compounds according to the invention the following intermediates are prepared: (IR) 5.6 - dimethyl - 3 - exo - [(tetrahydro - 2H- pyran - 2 - yl) - oxy]methyl - [5 - norbomen - 2- endomethanol] by the treatment of [(IR) 5,6- dimethyl - 3 - exo] - [(tetrahydro - 2H - pyran- 2 -yl) - oxy]methyl - (5 - norbornen - 2 - endoyl) - methyl (IR) - 2 - exo - bornane carbamate with KOH/CH 3 OH in Example 12 (see also Examples 31 and 44); (IR)-5,6-dimethyl-3-exo- [(tetrahydro - 2H - pyran - 2 - yl)oxy]methyl - 5- norbornen - 2 - endo - yl - methyl - methane sulphonate is prepared by treating the corresponding hydroxy compound with CH 3 SO 2 Cl in Example 13 (see also Example 32); (IR)-5,6- dimethyl - 3 - endo - [(methylsulphonyl) - oxy] methyl - 5 - norbornen - 2 - endo - yl - methyl (IR) 2 - oxo - bornene - carbamate is prepared by treating [(IR)-3-endo-hydroxymethyl-5,6-dimethyl - 5 - norbornen - 2 - endo - yl]methyl (IR) - 2 - exobornane carbamate with CH 3 SO 2 Cl, in Example 14; (3-exo-formyl-5,6- dimethyl - 5 - norbornene - 2 - endo - yl) - methyl methyl phthalate is prepared by treating (3- acetoxymethylene - 5,6 - dimethyl - 5 - norbornen - 2 - endo - yl) - methyl methyl phthalate with H 2 S0 4 in Example 27 (see also Examples 25, 28, 40 and 41); (3aR,4S,5R,6aS)-4- benzyloxymethyl - hexahydro - 5 - hydroxy - 2H- cyclopenta[b]furan is obtained by treating (1S,3R,5S,5R) - 4 - benzyloxymethyl - 5 - [(1- pyrrolidinyl - carbonyl) -methyl] - 1,3 - cyclopentylene - diacetate with alcoholic KOH, in Examples 24; 5,6-dimethyl-3-exo-tetrahydropyran - 2 - yl) - oxymethyl - 5 - norbornen - 2- endo-acetonitrile is prepared by treating 5,6- dimethyl - 3 - exo - (tetrahydro - 2H 8 pyran - 2- yl) - oxymethyl - 5 - norbornen - 2 - endo - ylmethyl with NaCN in Example 33; 3- exo - (hydroxymethyl) - 5,6 - dimethyl - 5 - norbornen - 2 - endo - acetonitrile is obtained by the reaction of the product of Example 33 with CH 3 OH/HCl in Example 34; 3-exo-(benzyloxy)- methyl - 5.6 - dimethyl - 5 - norbornen - 2 - endoacetonitrile is obtained by treating the product of Example 34 with monoglyme in Example 35; 3α,5α - diacetyl - 2# - benzyloxymethyl - lα - cyclopentane acetonitrile is prepared by ozonizing the product of Example 35 at -70‹ C. in Example 36; 4,4-benzyloxymethyl-5α-cyanomethyl - 1α,3α - cyclopentylene diacetate is prepared by the oxidation of the product of Example 36 with trifluoro-peracetic acid in Example 37. The intermediates described in Examples 14-23 are described in the Specifications 1,439,543 and 1,439,544.
GB4052973A 1972-08-28 1973-08-28 Derivatives of norbornene Expired GB1439542A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1268472A CH585163A5 (en) 1972-08-28 1972-08-28

Publications (1)

Publication Number Publication Date
GB1439542A true GB1439542A (en) 1976-06-16

Family

ID=4385437

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4052973A Expired GB1439542A (en) 1972-08-28 1973-08-28 Derivatives of norbornene

Country Status (8)

Country Link
JP (1) JPS4956963A (en)
AT (1) AT336561B (en)
BE (1) BE804053A (en)
CH (1) CH585163A5 (en)
DE (1) DE2342462A1 (en)
FR (1) FR2224455B1 (en)
GB (1) GB1439542A (en)
NL (1) NL7311023A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6227613A (en) * 1985-07-29 1987-02-05 Nippon Kogaku Kk <Nikon> Position detector
JP2014185124A (en) * 2013-03-25 2014-10-02 Arakawa Chem Ind Co Ltd Method of producing exo-type norbornene compound

Also Published As

Publication number Publication date
BE804053A (en) 1974-02-27
DE2342462A1 (en) 1974-03-14
FR2224455A1 (en) 1974-10-31
FR2224455B1 (en) 1978-09-29
CH585163A5 (en) 1977-02-28
JPS4956963A (en) 1974-06-03
ATA742773A (en) 1976-09-15
AT336561B (en) 1977-05-10
NL7311023A (en) 1974-03-04

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee