Iodoethane → HCID 68558057, compound

Participants

Reaction Conditions

Reaction Steps

Slowly add lithium hexamethyldisilazide (2.28 mL, 2.28 mmol, 1.0 M in tetrahydrofuran) at −78° C. under nitrogen to a solution of (R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-oxomorpholine-4-carboxylic acid tert-butyl ester) (1 g, 1.52 mmol) and iodoethane (1.24 mL, 15.2 mmol) in anhydrous tetrahydrofuran (10 mL). Stir at −78° C. for 45 minutes, remove the bath and stir for 1.5 hours. Add water and ethyl acetate. Separate the organic layer and extract the aqueous layer with ethyl acetate. Combine the organic layers, dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 90:10 hexane:ethyl acetate) to give the desired compound as a white solid (848 mg, 82%).

Provenance & Evidence