J. Mukherjee
Jul 15, 1990
Citations
0
Influential Citations
9
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract Diethylaminosulfur trifluoride (DAST) was used to prepare 2,6-dimethoxybenzoyl fluoride, which on reaction with (S)-N-ethyl-2-aminomethylpyrrolidine gave (S)-N- [(1-ethyl-2-pyrrolidinyl)methyl]-2,6-dimethoxybenzamide in >95% yields. A three- step efficient synthesis of the fluorinated benzamide neuroleptic, (S)-N-[(1-ethyl-2- pyrrolidinyl)methyl]-5-(3-fluoropropyl)-2-methoxybenzamide was then carried out using DAST in an essential step. 3-(4-Methoxyphenyl)-1-propanol was converted to 5- (3-hydroxypropyl)-2-methoxybenzoic acid with n-butyllithium and CO2 in 80–90% yields. The acid was then reacted with DAST to provide 5-(3-fluoropropyl)-2- methoxybenzoyl fluoride, which was then treated with (S)-N-ethyl-2- aminomethylpyrrolidine to give the fluorinated benzamide in >90% yields.