Potassium bis(trimethylsilyl)amide → (1-(S)methyl-allyl)-carbamic acid benzyl ester

Participants

Reaction Conditions

Reaction Steps

Methyltriphenylphosphonium bromide (16.92 g, 47.30 mmol) was taken up in toluene (350 mL). The heterogeneous solution was cooled to 0° C. then KHMDS 0.5M in toluene (90 mL, 45 mmol) was added. The reaction was stirred at 0° C. for 30 min, then cooled to −78° C. and (1-(S)-methyl-2-oxo-ethyl)-carbamic acid benzyl ester (6.11 g, 29.56 mmol) that was dissolved in toluene (45 mL) was added. The solution was warm to rt, stirred at it for 30 min, then quenched with sat NH4Cl(aq) (150 mL). The layers were separated and the aqueous was washed with EtOAc. The organics were combined and dried over Na2SO4. Solids were removed by filtration and solvent removed under reduced pressure. (1-(S)-methyl-allyl)-carbamic acid benzyl ester (4.90 g, 81%) was isolated by silica gel chromatography as a colorless oil.

Provenance & Evidence