4-Toluenesulfonyl chloride → HCID 86585070, compound

Participants

Reaction Steps

4.7 g (15.7 mmol) (2S,4R)-4-Hydroxy-2-(piperidin-1-ylcarbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester in 300 ml CH2Cl2 were treated with 4.5 g (23.6 mmol, 1.5 eq) p-toluene sulfonylchloride in the presence of 2.88 g (23.6 mmol, 1.5 eq) DMAP at RT for 48 h. The solution was washed with 1M KHSO4, water, 5% aq. NaHCO3 solution, water and brine, dried over Na2SO4 and was concentrated. Flash chromatography yielded 6.42 g (90%) (2S,4R)-2-(Piperidine-1-carbonyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester as white foam.

Provenance & Evidence