Allyl bromide → Methyl (2S)-2-[(1S)-1-[(tert-butoxycarbonyl)amino]-2-oxo-2-pyrrolidin-1-ylethyl]pent-4-enoate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of the product from Step A (2.05 g, 6.83 mmol) in THF (30 mL) was added potassium hexamethyldisilazide (30.0 mL, 0.5M in toluene, 15.0 mmol) at −78° C. The resulting mixture was stirred at −78° C. for 30 min. Allyl bromide (3.0 mL, 34.7 mmol) was then added. After stirring at −78° C. for 2 h, the reaction was quenched with saturated aqueous ammonium chloride solution. The organic phase was separated and the aqueous phase was extracted with two portions of ethyl acetate. The combined organic layers were washed with brine and concentrated in vacuo. Purification by flash chromatography (30:70 hexanes/ethyl acetate) afforded the desired product (major diastereoisomer from the reaction).

Provenance & Evidence