Lithium Hexamethyldisilazide → (R)-4-Benzyl-3-[(S)-2-(3,5-dichloro-4'-fluoro-biphenyl-4-ylmethyl)-pent-4-enoyl]-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

Dissolve (R)-4-Benzyl-3-pent-4-enoyl-oxazolidin-2-one (3.86 mmoles; 1.00 g) in THF (2 mL) and cool the mixture in a dry ice acetone bath. Add Lithium Bis(trimethylsilyl)amide (4.24 mmoles; 4.24 mL) dropwise at −78° C. under nitrogen. Stir the mixture at −78° C. for 10 minutes, and then warm to −25° C. for 1 hour. Cool the mixture back down to −78° C. and add 4-Bromomethyl-3,5-dichloro-4′-fluoro-biphenyl (4.43 mmoles; 1.48 g) in THF (2 mL) dropwise at −78° C. Warm the reaction to ambient temp. After stirring overnight, the LCMS analysis indicated 2 peaks. Purify the mixture over silica gel using hexane to 1:1 EtOAc/hexanes to obtain 1.3 g oil/foam. WY=65.8%, LCMS=89.6% (M+1=512.0).

Provenance & Evidence