tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylate → (S)-N-Boc-2-methylpyrrolidine

Participants

Reaction Steps

To a solution of 2-(S)-(toluene-4-sulfonyloxymethyl)-pyrrolidine- 1-carboxylic acid tert-butyl ester (compound (4), 1.77 g, 4.99 mmol) in 5 mL of THF at 0° C. was added dropwise 15 mL (15 mmol) of a 1 M THF solution of lithium triethylborohydride. After 15 hours, the reaction was quenched by addition of 7.39 mL of water. The reaction was diluted with 35 mL of chloroform, and poured into a separatory funnel. The mixture was diluted with dichloromethane and washed with saturated aqueous NaCl solution. The organic phase then was dried over sodium sulfate. The mixture was concentrated in vacuo and purified by flash chromatography on silica gel, eluting with 1:3 ethyl acetate/hexane to give pure product as a clear oil (0.73 g, 79% yield).

Provenance & Evidence