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

Temperature

0 °C

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.

1. temperaturecooled to −78° C.
2. additionwas added
3. temperatureThe solution was warm to rt
4. stirringstirred at it for 30 min
5. customquenched with sat NH4Cl(aq) (150 mL)
6. customThe layers were separated
7. washthe aqueous was washed with EtOAc
8. dry with materialdried over Na2SO4
9. customSolids were removed by filtration and solvent
10. customremoved under reduced pressure

ORD record

ord-ce90f49f010942558fdcb0ee3e6a2a2b

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569302B2