Water → HCID 58331114, compound

Participants

Reaction Steps

0.98 g (4 mmol) of 1-tert-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dioate (ALDRICH) was dissolved in 36 ml of 1,2-dibromoethane and cooled in an ice-bath. After addition of 1.36 g (4 mmol) of tetrabutylammonium bisulphite, 18 ml of 50% strength aqueous sodium hydroxide solution are added, and the mixture is stirred on ice for 2 hours and at room temperature overnight. After addition of 200 ml of water and 200 ml of dichloro-methane, the organic phase was washed once more with water, dried over sodium sulphate and filtered, and the filtrate was concentrated. The resulting crude product is chromatographed on silica gel using a dichloromethane/ethyl acetate gradient, and the appropriate fractions are combined and concentrated. Yield: 60 mg (4.3%)

Provenance & Evidence