Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → 1-Benzyl-4-methyl-pyrrolidine-3-carboxylic acid methyl ester

Participants

Reaction Steps

To a solution of N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (1.8 mL, 7 mmol) and methyl crotonate (0.62 mL, 5.8 mmol) in DCM (25 mL) at 0° C. was added dropwise a solution of trifluoroacetic acid (0.045 mL, 0.58 mmol) in DCM (1 mL). The reaction was allowed to warm to room temperature and was stirred for 3 h. Saturated sodium bicarbonate solution was added and the phases were separated. The aqueous phase was extracted twice with DCM and the combined organics were dried over sodium sulfate and concentrated in vacuo. This yielded crude methyl rac-(trans)-4-methyl-1-(phenylmethyl)-3-pyrrolidinecarboxylate (1.58 g) which was used without further purification. LCMS: (M+H)+: 234.3.

Provenance & Evidence