C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/361.2, 260/3
C07D 493/08 (2006.01) C07D 493/18 (2006.01)
Patent
CA 1212681
ABSTRACT METHOD FOR PRODUCING INTERMEDIATES USEFUL IN THE PREPARATION OF 7-OXABICYCLOHEPTANE PROSTAGLANPIN DERIVATIVES A method is provided for preparing intermediates for use in preparing 7-oxabicyclo- heptane prostaglandin derivatives which method includes the steps of reducing (exo)hexa hydro- 4,7-epoxyisobenzofuran-1,3-dione to the corresponding diol, subjecting the diol to a chloroformylation reaction to form a compound of the structure Image reacting the above with pyridine to form the cyclic carbonate of the structure Image reacting the cyclic carbonate with an alkanol to form the alcohol of the structure Image tosylating the above alcohol to form the tosylate Image and subjecting the above tosylate to a cyanation reaction to form the cyano carbonate of the structure Image The cyano carbonate may then be reduced by, for example, reaction with diisobutyl aluminum hydride to form the hemiacetal Image which is used in preparing 7-oxabicyclo heptane prostaglandin derivatives as disclosed in U. S. Patent No. 4,143.054. New intermediates of the structures set out above, other than the hemiacetal, are also provided.
465074
Das Jagabandhu
Haslanger Martin F.
Osler Hoskin & Harcourt Llp
Squibb (e.r.) & Sons Inc.
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