GB868483A - New intermediates in the synthesis of reserpine and their preparation - Google Patents

New intermediates in the synthesis of reserpine and their preparation

Info

Publication number
GB868483A
GB868483A GB13236/59A GB1323659A GB868483A GB 868483 A GB868483 A GB 868483A GB 13236/59 A GB13236/59 A GB 13236/59A GB 1323659 A GB1323659 A GB 1323659A GB 868483 A GB868483 A GB 868483A
Authority
GB
United Kingdom
Prior art keywords
carboxylic acid
hydroxy
laevo
oxo
hexahydronaphthalene
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
GB13236/59A
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.)
Laboratoires Francais de Chimiotherapie SA
Original Assignee
Laboratoires Francais de Chimiotherapie SA
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 Laboratoires Francais de Chimiotherapie SA filed Critical Laboratoires Francais de Chimiotherapie SA
Publication of GB868483A publication Critical patent/GB868483A/en
Expired legal-status Critical Current

Links

Landscapes

  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises (a) dextro- and laevo- 5b -hydroxy-8-oxo-1,4,4aa ,5,8, 8aa -hexahydronaphthalene-1b -carboxylic acid, their salts with optically active bases, e.g. quinine, bromine, cinchonine and laevoephedrine, (b) laevo- 1,8,-lactone of 5b -hydroxy-8-oxo-1,4, 4aa ,5,8,8aa - hexahydronaphthalene- 1b - carboxylic acid (c) the laevo- 1,8-lactone of 5b ,8b -dihydroxy- 1,4,4aa ,5,8, 8aa - hexahydronaphthalene-1b -carboxylic acid, (d) the dextrolactone of 8b -hydroxy-2a -methoxy-3b ,5b -epoxy-1,2,3, 4,4aa ,5,8,8aa - octahydronaphthalene- 1b - carboxylic acid, (e) laevo- 3-hydroxy-2a -methoxy-7- oxo- 1,2,3,4,4aa ,7,8, 8aa - octahydronaphthalene-1-carboxylic acid, (f) its laevomethyl ester and (g) its laevomethyl ester 3-acetate, together with processes for their preparation. Compounds (a) are prepared by optical resolution of the corresponding racemate, (b) is formed by lactonisation of the dextro- (a) with sodium acetate and acetic anhydride in methylene chloride, (c) by reduction of (b) with aluminium isopropylate in isopropanol, (d) by treating the dextrolactone of 8b -hydroxy-2a - bromo-3b ,5b -epoxy- 1,2,3,4,4aa , 5,8,8aa - octahydronaphthalene- 1b - carboxylic acid with sodium methoxide in methanol, (e) by reducing laevolactone of 6a -bromo-8b -hydroxy-2a - methoxy-3b ,5b - epoxy-7- oxo-4aa , 8aa - decahydronaphthalene-1b - carboxylic acid with zinc powder in a solvent, (f) by esterification of (e) with diazomethane and (g) by acetylation of (f) with acetic anhydride in a tertiary base. Detailed examples are given.
GB13236/59A 1956-10-31 1957-10-30 New intermediates in the synthesis of reserpine and their preparation Expired GB868483A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR868483X 1956-10-31

Publications (1)

Publication Number Publication Date
GB868483A true GB868483A (en) 1961-05-17

Family

ID=9346158

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13236/59A Expired GB868483A (en) 1956-10-31 1957-10-30 New intermediates in the synthesis of reserpine and their preparation

Country Status (1)

Country Link
GB (1) GB868483A (en)

Similar Documents

Publication Publication Date Title
GB799271A (en) Production of intermediates for the synthesis of reserpine and allied compounds
SE7705637L (en) PROCEDURE FOR THE PREPARATION OF DIBENSOXEPIN DERIVATIVES WITH THERAPEUTIC EFFECT
GB868483A (en) New intermediates in the synthesis of reserpine and their preparation
GB1382121A (en) Polybasic ether carboxylic acids
GB1294649A (en) Perfluoralkylmonocarboxylic acid esters, processes for their manufacture and their use
GB908986A (en) Sulphur-containing dicarboxylic acids and derivatives thereof and a process for the manufacture of same
GB888417A (en) Syntheisis of new reserpine intermediates
ES395599A1 (en) Orally administered contrast agents for cholecystography
GB835823A (en) New derivatives of diphenyl ether and their production
ES269514A1 (en) Ethers of methyl 18-epi-reserpate and salts thereof and process for their manufacture
GB796311A (en) Improvements in or relating to esters of spiramycins
GB1198414A (en) Process for the Preparation of 4-acyloxybutyric Acid Esters
IT1024395B (en) PROCEDURE FOR PRODUCING ETHYL ESTER OF ACID 2 ACETOACETYL AMINOTHIAZOLIL 4 ACETIC
GB811816A (en) Heterocyclic hydrazides
IT1064799B (en) PROCEDURE FOR THE PRODUCTION OF ALCOHOL WITH HIGH YIELDS FROM CELLULOSE MATERIALS
ES408943A1 (en) Unsaturated esters and thio-esters and insect control
GB970789A (en) Process of esterification
GB856361A (en) 4-methyl-17ª‡-hydroxyprogesterone and its esters and their preparation
ES458443A1 (en) Procedure for obtaining acids, 3-pi-hydroxy-11-alpha-alcoxy-olean-12-in-30-oicos and their steres. (Machine-translation by Google Translate, not legally binding)
FR1197637A (en) Process for the production of cysteine ester derivatives and novel derivatives which can be prepared by this process
GB1432308A (en) Process for the preparation of acetone dicarboxylic acid and derivatives thereof and of citric acid semiconductor structures
GB868488A (en) Improvements in or relating to reserpine compounds
GB729617A (en) Process for the synthesis of chloramphenicol
GB823707A (en) Isoreserpic acid and esters thereof and processes for their manufacture
CA529986A (en) PREPARATION OF .alpha.-ACYLAMIDO ACETIC ESTERS