1,1'-Carbonyldiimidazole → [1-Methyl-2-[[(3-methyl-1-(phenylmethyl)-3-pyrrolidinyl)methyl]amino]-2-oxoethyl]carbamic acid, 1,1-dimethylethyl ester

Participants

Reaction Steps

A solution of 14.1 g (75 mmole) of t-butoxycarbonyl-L-alanine in 135 ml of dry acetonitrile was treated with 12.5 g (77 mmol) of 1,1'-carbonyldiimidazole. After stirring at room temperature for one hour and gas evolution had ceased, the reaction mixture was heated at 60° for one hour cooled to room temperature and treated with 14.2 g (70 mmol) of 3-methyl-1-(phenylmethyl)-3-pyrrolidinemethanamine. The reaction mixture was stirred at room temperature for 18 hours and the solvent was removed in vacuo. The residue was partitioned between ethyl acetate/water and the organic layer was separated, washed with water, dried (MgSO4), and evaporated in vacuo to give 23.9 g of the title compound.

Provenance & Evidence