Benzyl Bromide → HCID 59166764, compound

Participants

Reaction Steps

(2S,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (CAS Reg. No. 227935-38-8)(300 mg, 1.2 mmol) and 60% sodium hydride mineral oil dispersion (61 mg, 1.5 mmol) were dissolved in anhydrous dimethylformamide (9 ml) at 0° C. under a nitrogen atmosphere. After 10 mins stirring benzylbromide (0.153 ml, 1.3 mmol) in CH2Cl2 (1 ml) was added drop wise and the reaction mixture stirred to room temperature for 1 hour. The solvent was removed under reduced pressure and the residue dissolved in ethyl acetate (25 ml), washed with water (2×25 ml), dried (magnesium sulphate), filtered and evaporated under reduced pressure. The residue was purified using flash chromatography eluting with a solvent gradient 4:1 heptane:ethyl acetate, yielding the title compound (167 mg, 42% yield) as an oil.

Provenance & Evidence