Benzyl Bromide → HCID 19705487, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 3-(2-methylpropyl)-2-oxo-3-(propen-2-yl)-1-pyrrolidineacetate (Example 20, step 5; 1.63 g, 6.10 mmol) and THF (15 mL) is cooled to -78° C. and LDA (2.0M, 3.2 mL, 6.4 mmol) is added. The solution is stirred at -78° C. for 30 minutes and then benzyl bromide (0.80 mL, 6.7 mmol) is added. The solution is allowed to warm to 0° C. over 2 hours, and then stirred at 0° C. for 1 hour. After quenching with saturated aqueous ammonium chloride (10 mL), aqueous workup (EtOAc, MgSO4) and purification by column chromatography (10% EtOAc/hexane) provided 1.94 g (89%) of the title compound as an oil in a 1:1 mixture of diastereomers.

Provenance & Evidence