Water → (S)-tert-Butyl 3-methoxypyrrolidine-1-carboxylate

Participants

Reaction Steps

Sodium hydride (2.2 g, 80% dispersion in mineral oil, 73.2 mmol) was added to an ice-cooled solution of (3S)-N-tert-butoxycarbonylpyrrolidin-3-ol (U.S. Pat. No. 6,180,627 preparation 78), (12.5 g, 66.7 mmol) in tetrahydrofuran (330 ml), and the solution was stirred at room temperature for an hour. Iodomethane (14.5 g, 100 mmol) was then added and the reaction stirred for 18 hours. Water (100 ml) was added and the mixture concentrated under reduced pressure to remove the organic solvents. The solution was partitioned between water (750 ml) and ethyl acetate (750 ml) the layers separated, and the organic solution dried over magnesium sulphate and evaporated under reduced pressure to give the title compound.

Provenance & Evidence