GB888411A - Esterification of yohimbane derivatives - Google Patents

Esterification of yohimbane derivatives

Info

Publication number
GB888411A
GB888411A GB11639/58A GB1163958A GB888411A GB 888411 A GB888411 A GB 888411A GB 11639/58 A GB11639/58 A GB 11639/58A GB 1163958 A GB1163958 A GB 1163958A GB 888411 A GB888411 A GB 888411A
Authority
GB
United Kingdom
Prior art keywords
yohimbane
methoxycarbonyl
esterification
trimethoxybenzoyloxy
seco
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
GB11639/58A
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 GB888411A publication Critical patent/GB888411A/en
Expired legal-status Critical Current

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Abstract

18b -Hydroxy-20a -yohimbane esters having the following structure at carbon atoms 16, 17, and 18 <FORM:0888411/IV (b)/1> wherein R is alkyl, aryl, aralkyl, or alkaryl, and R1 is -OCH3 or -CN, are prepared by esterification of the corresponding 18b -hydroxy compounds with the appropriate acid anhydride in the presence of a pyridine base and a second organic tertiary base stronger than pyridine, e.g. triethylamine, with warming and in the absence of air. Examples describe the preparation of reserpine, rescinnamine, deserpidine, 18b -(31,41,51 - trimethoxybenzoyloxy) - 17a - methoxy16b - methoxycarbonyl - 3 - oxo - 2,3 - seco - 20a - yohimbane, and its 11-methoxy derivative, 18b -(31,41,51 - trimethoxycinnamoyloxy) - 11,17a - dimethoxy - 16b - methoxycarbonyl - 3 - oxo - 2,3 - seco - 20a - yohimbane, 10 - chlorodeserpidine, and laevo - 18b - (31,41,51 - trimethoxybenzoyloxy) - 11 - methoxy - 18b - methoxycarbonyl - 17a - cyano - 3b ,20a - yohimbane. 3,4,5-Trimethoxycinnamoyl anhydride is prepared from the acid by treatment with tosyl chloride and triethylamine in acetone. Specifications 809,912, 868,475, 868,477, 888,407, 888,408, 888,409, 888,410, 888,412, 888,413, 888,414 and 888,418 are referred to.
GB11639/58A 1957-07-25 1958-04-11 Esterification of yohimbane derivatives Expired GB888411A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR888411X 1957-07-25

Publications (1)

Publication Number Publication Date
GB888411A true GB888411A (en) 1962-01-31

Family

ID=9376762

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11639/58A Expired GB888411A (en) 1957-07-25 1958-04-11 Esterification of yohimbane derivatives

Country Status (1)

Country Link
GB (1) GB888411A (en)

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