Sodium hydride → 4-(4-Chlorophenylsulfonylamino)pyrrolidine

Participants

Reaction Steps

To a solution of (4-carboxybutyl)triphenylphosphonium bromide (17.3 g) in dimethyl sulfoxide (45 ml) was added sodium methylsulfinylmethide [78.0 m mol, prepared from sodium hydride (3.12 g) and dimethyl sulfoxide (45 ml)] and the solution was stirred at room temperature for 20 minutes. To the resulting solution was added (2S,4R)-1-t-butoxycarbonyl-4-(4chlorophenylsulfonylamino)-2-formylpyrrolidine (5.06 g) in dimethyl sulfoxide (30 ml) and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added water and the aqueous solution was washed with ethyl acetate. The aqueous phase was adjusted to pH 2 with 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed successively with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column with a mixture of chloroform and methanol (40:1) as an eluent to give (2S,4R)-1-t-butoxycarbonyl-2-[(E and Z)- 5-carboxy-1-pentenyl]-4-(4-chlorophenylsulfonylamino) pyrrolidine (7.64 g) as a pale brown oil.

Provenance & Evidence