Water → HCID 54185742, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (3R)-N-tert-butyloxycarbonylpyrrolidin-3-ol (2.00 g, 10.7 mmol) in anhydrous DMF (12 ml) was added dropwise to a stirred slurry of sodium hydride (60% dispersion in oil, 0.465 g, 11.6 mmol) in DMF (25 ml) at -10° C. under nitrogen and the mixture stirred at this temperature for 0.67 h. 4-Methoxybenzyl chloride (1.52 ml, 11.2 mmol) was added dropwise and the mixture warmed to 0° C. over 1 h and then stirred at RT for 2 h. Water was added and the mixture poured into ether and washed with water (×3). The ethereal layer was dried (MgSO4), evaporated in uacuo and the crude product chromatographed on silica gel, eluting with ethyl acetate/hexane (30:70), to afford the title pyrrolidine (3.09 g, 94%),δ (250 MHz, CDCl3) 1.46 (9H, br s, OC(Me)3), 1.73-2.09 (2H, m, CH2), 3.40-3.46 (4H, m, 2 of CH2), 3.81 (3H, s, OMe), 4.12 (1H, m, CHOCH2Ar), 4.45 (2H, s, OCH2Ar), 6.85-6.91 (2H, m, Ar--H), 7.23-7.27 (2H, m, Ar--H).

Provenance & Evidence