Water → HCID 15016533, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3R)-1-[(R)-1-phenylethyl]-3-(hydroxymethyl)pyrrolidine (25.2 g, 0.12 mol) in CH2Cl2 (250 mL) was added Et3N (18.8 mL, 0.13 mol). The mixture was cooled to 0° C. and treated dropwise with methanesulfonyl chloride (10.63 mL, 0.13 mol) dissolved in CH2Cl2 (125 mL). The mixture was stirred at 0° for 1.5 hours and then at 25° C. for 4 hours. Water was added and the organic layer was separated, washed with NaHCO3 (2×), dried (MgSO4) and concentrated to provide (3R)-1-[(R)-1-phenylethyl]-3-(methanesulfonyl methyl)pyrrolidine (2a, 33.2 g); NMR (CDCl3) δ1.39 (m, 3 H), 1.54 (m, 1 H), 2.0 (m, 1 H), 2.3-2.8 (m, 5H), 2.98 (d, 3 H), 3.29 (q, 1 H), 4.14 (t, 2 H), 7.31 (m, 5 H). The material was used directly in the next step.

Provenance & Evidence