Allyl bromide → HCID 19705440, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl N-tert-butyloxycarbonyl-3-(2-methylpropyl)-2-oxo-3-pyrrolidineacetate (3.65 g, 10.3 mmol) in dry THF (45 mL) is cooled to -78° C. and treated drop-wise with LDA (5.70 mL, 11.3 mmol). After 30 minutes at -78° C., allyl bromide (1.10 mL, 12.4 mmol) is added. The solution is maintained at -78° C. for 3 hours, and is then allowed to slowly warm to room temperature under N2. After 12 hours, the solution is quenched with saturated NH4Cl (10 mL) and diluted with H2O (50 mL). The crude lactem is extracted into EtOAc (3×100 mL). The organic extracts are combined, washed with brine (50 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 4.72 g of gold oil. The oil is purified by silica gel chromatography (300 g SG, 5% EtOAc/hexane) to yield 2.98 g (73%) of the title compound as a clear, pale gold oil as a mixture of diastereomers.

Provenance & Evidence