Dimethyl Sulfoxide → HCID 86584831, compound

Participants

Reaction Steps

To 4.2 ml (48.65 mmol, 1.2 eq) oxalyl chloride in 100 ml CH2Cl2 were added 6.5 ml (89.19 mmol, 2.2 eq) DMSO in 20 ml CH2Cl2 at −65° C., followed after 10 min by 14.33 g (40.54 mmol, 1.0 eq) (2S,4R)-2-hydroxymethyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester in 60 ml CH2Cl2 over a period of 20 min. The solution was stirred at −68° C. for 1.5 h before 28 ml (162.16 mmol, 4 eq) iPr2NEt were added, and the reaction mixture was warmed to room temperature. The solution was extracted with 1M KHSO4, the combined inorganic phases were extracted with CH2Cl2 and the organic phase dried over Na2SO4 and evaporated, yielding 14.18 g (99%) (2S,4R)-2-formyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester. The crude product was subjected to the following reaction without further purification.

Provenance & Evidence