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O-Alkylation Using Ag2O; Synthesis of Novel 4-Alkyloxy-2-phenylcarboxamidyl-1-tosylpyrrolidines
O-Alkylation Using Ag2O; Synthesis of Novel 4-Alkyloxy-2-phenylcarboxamidyl-1-tosylpyrrolidines
Journal of the Korean Chemical Society. 2001. Dec, 45(6): 549-554
  • Published : December 00, 2001
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Park, Myeong Suk

Abstract
For the development of new COX-2 inhibitor, novel compound were synthesized through induction an arylsulfonyl group to 1-position, an arylcarboxamidyl group to 2-position and an alkyl group to 4-position of L-proline. We started from 4-hydroxy-L-proline, the 4-methylphenylsulfonyl of 1-position was introduced through N-tosylation and the carboxylic acid group was protected by esterification. We sucessfully converted to a various derivatives 4b-d for O-alkyl-(or aralkyl)ation of 4-position using silver oxide as catalysis. The 4-alkyloxy-1-tosyl L-prolines 5b-d were synthesized through base-hydrolysis for the deprotection of carboxylic acid. Final compound 1,2,4-substituted pyrrolidines, 4-alkyloxy-2-phenylcarboxamidyl-1-tosyl pyrrolidines 6a-d were synthesized through the condensation of arylamine with 3 and 5b-d using DCC.??????????