Trifluoroacetic acid → 1-Benzyl-4-[(S)-2-(tert-butyldimethylsilyloxy)-1-(methyl)ethyl]pyrrolidine-3-carboxylic acid methyl ester

Participants

Reaction Steps

N-Benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (2.97 mL, 11.6 mmol) was added to a solution of (E)-(S)-5-(tert-butyldimethylsilyloxy)-4-methylpent-2-ene acid methyl ester (2.5 g, 9.67 mmol) in dichloromethane (20 mL), and then a trace amount of trifluoroacetic acid was added. The mixture was stirred for 30 minutes and then saturated sodium bicarbonate water was added. The organic layer was separated and dried over magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give 3.0 g (78%) of the diastereomer mixture title compound as a colorless oil. The diastereomers were used for the next step without separation.

Provenance & Evidence