3,4,5-Trimethoxybenzoic Acid → N-Boc-pyrrolidine

Participants

Reaction Steps

Experimental condition analogous to Example 22 were used with 2-(R)-[(2-methyl-3-phenyl-allylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (prepared according to the scheme 13) were used with 2-(R)-carboxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester) 0.5 g (1.51 mmol), 3,4,5-trimethoxy benzoic acid 0.38 g (1.8 mmol), triethylamine 0.1 ml, 1-(dimethylaminopropyl)-3-ethylcarbodiimide 0.43 g (2.2 mmol), and 1-hydroxybenzotriazole 0.2 g (1.5 mmol) in 10 ml DCM. The reaction yielded 0.46 g of 2-(R){[2-methyl-3-phenyl-allyl)-3,4,5-trimethoxy-benzoyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester. After BOC deprotection analogous to the Example 13, the compound was transformed to the HCl salt, 0.35 g of a white solid was obtained. Yield: 50%

Provenance & Evidence