Water → (R)-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 (3R)-N-tert-butoxycarbonylpyrrolidin-3-ol (J. Med. Chem. 41; 25; 1998; 4983) (12.5 g, 66.7 mmol) in tetrahydrofuran (330 ml), and the solution stirred at room temperature for an hour. Methyl iodide (14.5 g, 100 mmol) was then added and the reaction stiired for 18 hours. Water (100 ml) was added and the mixture concentrated under reduced pressure to remove the organic solvents. The aqueous was extracted with ethyl acetate, the combined organic solutions dried (MgSO4) and evaporated under reduced pressure to give the title compound as an oil, 12.48 g.

Provenance & Evidence