Title:
MANUFACTURE OF INTERMEDIATE COMPOUND
Document Type and Number:
Japanese Patent JPS5993070
Kind Code:
A
Abstract:
1396207 Cyclopenta[b]furan derivatives UPJOHN CO 30 March 1973 [27 April 1972] 32008/74 Divided out of 1396206 Headings C2C and C2P The invention comprises optically active cyclopenta[b]furan derivatives of the formula or racemates thereof, wherein C n H 2n is C 1-9 alkylene, with 1 to 6 carbon atoms in the chain -CFR 2 - and terminal CH 3 , and either M is or and R 6 is H or 2-tetrahydropyranyl, or M is = O, and R 6 is R 3 , wherein R 3 is benzoyl or naphthoyl optionally substituted 1 to 5 times by C 1-4 alkyl, C 7-10 phenylalkyl, or NO 2 , provided that not more than two of the substituents are other than alkyl, and the total number of carbon atoms in the substituents does not exceed 10, C 2-5 alkoxycarbonylbenzoyl, or acetyl and their preparation. Compounds of the above formula in which M is and R 6 is 2-tetrahydropyranyl are prepared by etherifying the corresponding compounds in which R 6 is H, obtained by hydrolysing the appropriate compounds in which M is and R 6 is R 3 , which are made by reducing the compounds in which M = O, resulting from treating the corresponding 5α - acyloxy - 4#- formyl - 3,3a#,4,5,6,6a# - hexahydro - 2H- cyclopenta[b]furan-2-ones with anions of phosphonates of the formula wherein R 5 is C 1-8 alkyl. 5α - Benzoyloxy - 4# - formyl - 3,3a#,4,5,6,6a#- hexahydro - 2H - cyclopenta[b]furan - 2 - one is prepared by oxidizing 5α-benzoyloxy-4#-hydroxymethyl - 3,3a#,4,5,6,6a# - hexahydro - 2H - cyclopenta[b]furan, resulting from the demethylation of the corresponding 4#-methoxymethyl compound, which is obtained by deiodinating 5α- benzoyloxy - 6 - iodo - 4# - methoxymethyl - 3,3a#, 4,6,6,6a# - hexahydro - 2H - cyclopenta[b]furan-2- one, resulting from the benzoylation of the corresponding 5α-hydroxy compound. Methyl 2,2-difluorohexanoate is obtained by reacting methyl 2-oxohexanoate with MoF 6 .BF 3 . Dimethyl 2 - oxo - 3 - fluoroheptylphosphonate dimethyl 2 - oxo - 3 - fluoropentylphosphonate, dimethyl 2 - oxo - 3,3 - difluoro - 4 - methyloctylphosphonate and dimethyl - 2 - oxo - 3,3 - difluoroheptylphosphonate are obtained by reacting dimethyl methylphosphonate with ethyl 2- fluorohexanoate, methyl 2-fluorobutyrate, methyl 2,2 - difluoro - 3 - methylheptanoate and methyl 2,2-difluorohexanoate respectively.
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Inventors:
BAANII JIYON MAAGAAREIN
Application Number:
JP19842783A
Publication Date:
May 29, 1984
Filing Date:
October 25, 1983
Export Citation:
Assignee:
UPJOHN CO
International Classes:
A61K31/557; A61K31/5575; A61P43/00; C07C67/00; C07C401/00; C07C405/00; C07D307/935; C07D309/12; C07F9/40; C07F9/54; (IPC1-7): C07D307/935
Attorney, Agent or Firm:
Yataro Sasai