Pyridine → HCID 86600825, compound

Participants

Reaction Steps

A solution of 4-nitrobenzenesulfonyl chloride (4.44 g) in methylene chloride (50 ml) was added to a stirred solution of tert-butyl 3-(R)-hydroxypyrrolidine-1-carboxylate (3.75 g) and pyridine (2.5 ml) in methylene chloride (30 ml) at 10° C. and the mixture allowed to warm to ambient temperature with stirring. The reaction mixture was poured into saturated sodium bicarbonate solution. The organic layer was separated, washed with brine and dried over sodium sulfate. The solution was evaporated under vacuum to give tert-butyl3-(R)-[(4-nitrophenyl)sulfonyloxy]pyrrolidine-1-carboxylate as a yellow crystalline solid. (4.37 g, 59%); 1H NMR Spectrum: (CDCl3) 1.43 (s, 9H), 1.80-2.40 (m, 2H), 3.30-3.65 (m, 4H), 5.20 (hs, 1H), 8.10 (d, 2H), 8.42 (d, 2H).

Provenance & Evidence