2-Naphthalenesulfonyl chloride → HCID 131723839, compound

Participants

Reaction Steps

300 mg (1.17 mmol) (3S,5S)-Thioacetic acid S-[5-(piperidine-1-carbonyl)-pyrrolidin-3-yl] ester in 25 ml CH2Cl2 were treated with 398 mg (1.75 mmol, 1.5 eq) 2-naphthalene sulfonylchloride in the presence of 214 mg (1.75 mmol, 1.5 eq) DMAP at RT for 1.5 h. The solution was added to 1M KHSO4, the phases were separated and the inorganic extracted with CH2Cl2, the combined organic phases were washed with 1M KHSO4, water and brine, dried over Na2SO4 and were concentrated. Flash chromatography yielded 280 mg (54%) (3S,5S)-Thioacetic acid S-[1-(naphthalene-2-sulfonyl)-5-(piperidine-1-carbonyl)-pyrrolidin-3-yl] ester as white crystals.

Provenance & Evidence