Esters of 3-Pyrrolidinemethanol, processes for preparing them, Intermediates therefor, and Therapeutic Compositions containing them

摘要

1,197,573. 3-Pyrrolidinemethanol alkyl esters. A. H. ROBINS CO. Inc. 2 Aug., 1967 [8 Aug., 1966], No. 35567/67. Heading C2C. Novel esters of 3-pyrrolidinemethanol, of formula wherein R is hydrogen, lower alkyl, phenyl lower alkyl, substituted phenyl lower alkyl, cycloalkyl, phenoxy lower alkyl, phenyl-amino lower alkyl, phenyl, or substituted phenyl; R1 is hydrogen, lower alkyl, phenyl, phenyl lower alkyl, cycloalkyl, or substituted phenyl; R2 is phenyl or substituted phenyl; and R3 is lower alkyl, "lower" meaning C 1 -C 8 , cycloalkyl having 3-9 carbons, and substituted phenyl having one to three alkyl, alkoxy, halo, trifluoromethyl, and/or dialkylamino substituents, are prepared by esterification of the corresponding 3-pyrrolidinemethanol with an aliphatic acid anhydride. The 3-pyrrolidinemethanols are prepared from the corresponding 3-benzoyl or substituted benzoyl pyrrolidine, either by a Grignard reaction with the appropriate magnesium halide, R1MgX, or by reduction, or else by reduction of the corresponding 2-oxo-3-pyrrolidine methanol. The 2-oxo-3-pyrrolidine methanols are prepared by condensing a 1-substituted-2-pyrrolidinone with a ketone, R1COR2, in liquid ammonia with an alkali metal condensing agent. The 3 - benzoyl - pyrrolidine starting materials are obtained from a Grignard reaction of a 3-cyanopyrrolidine with a phenyl magnesium halide, R2MgX. Pharmaceutical compositions having analgesic properties comprise the novel esters with an oral or parenteral pharmaceutical carrier.