Methyl iodide → benzyl (2S,4R)-2-(fluoromethyl)-4-methoxypyrrolidine-1-carboxylate

Participants

Reaction Steps

To a solution of benzyl (2S,4R)-2-(fluoromethyl)-4-hydroxypyrrolidine-1-carboxylate (500 mg, 1.97 mmol) in THF (6.6 mL) at 0° C. was added methyl iodide (0.43 mL, 3.44 mmol) followed by sodium hydride (104 mg, 4.34 mmol). The mixture was stirred for 2 hours at room temperature. The reaction was quenched with ice, and diluted with diethyl ether. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford benzyl (2S,4R)-2-(fluoromethyl)-4-methoxypyrrolidine-1-carboxylate. MS ESI calc'd. for C14H18FNO3 [M+H]+ 268. found 268.

Provenance & Evidence