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

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Reaction Steps

N-Benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (16.6 mL, 65.0 mmol) was added to a solution of (E)-(R)-5-(tert-butyldimethylsilyloxy)-4-methylpent-2-ene acid methyl ester (14 g, 54.2 mmol) in methylene chloride (100 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 14.6 g (69%) of the diastereomer mixture title compound as a colorless oil. The diastereomers were used for the next step without separation.

Provenance & Evidence