Pyridine → tert-Butyl (2S)-2-(((4-methylbenzene-1-sulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

At a temperature of 0° C., p-toluenesulfonylchloride (6.0 g, 30.4 mol) was added portionwise to a stirred solution of (S)-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (4.9 g, 24.3 mmol) and pyridine (14.6 ml, 181 mmol) in dichloromethane (50 ml). The reaction mixture was stirred for 30 minutes at 0° C. and then allowed to stand for 15 hours at ambient temperature. Then dichloromethane (50 ml) was added. The solution was washed with water (4×50 ml) and saturated NaCl (50 ml) and then dried over Na2SO4. After evaporation of the solvent, the crude product (9.83 g in the form of an oil) was purified by flash chromatography over silica gel (eluent:cyclohexane/ethyl acetate 1:1) to afford 8.07 g (83.4% of theory) of (S)-2-(toluene-4-sulfonyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a colorless oil. 1H NMR (400 MHz, DMSO): δ 1.29 and 1.35 (s, 9H), 1.72 (m, 3H), 1.92 (m, 1H), 2.43 (s, 3H), 3.18 (m, 2H), 3.83 (m, 1H), 4.03 (m, 2H), 7.49 (d, 2H), 7.78 (d, 2H). MS [M+H]+ 256. [α]23D=−39.1 (c 5.98, CHCl3).

Provenance & Evidence