m-Chloroperbenzoic acid → HCID 86635431, compound

Participants

Reaction Steps

To 5-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (Ex. 4a, 490 mg, 0.94 mmol) in 10 mL of dichloromethane at room temperature under N2 was added m-chloroperbenzoic acid (247 mg, 1.1 mmol) in 5 portions during a period of 30 min. The resulting suspension was stirred for 3 h at room temperature and then the reaction was quenched by pouring the suspension onto ice (20 g). The mixture was extracted with ethyl acetate (2×40 mL) and the combined organic phase was dried over Na2SO4 and concentrated under reduced pressure. Chromatography (3-50% Ethyl acetate/hexanes) gave 5-[4-(3,5-di-tert-butyl-4-hydroxy-benzenesulfinyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester a white solid (480 mg, 95%). ESI/Cl-MS m/z 537 ([M−H]−).

Provenance & Evidence