Hydrogen Peroxide → Tert-butyl (3-hydroxy-2-methylpropyl)carbamate

Temperature

0 °C

The tert-butyl N-(2-methylallyl)carbamate (213 mg, 1.24 mmol) was diluted with THF (12 mL) and the mixture was cooled to 0° C. Borane-dimethylsulfide complex (0.9 mL, 1.8 mmol) was added. After 1.5 hours, the reaction was cooled to −40° C. and 1 N NaOH (5 mL) and 30% hydrogen peroxide (5 mL) were carefully added. After 15 minutes, the reaction was warmed slowly until the frozen mixture melted. Ethyl acetate (100 mL) was then added, and the mixture was washed with brine (3×10 mL). The combined aqueous layers were extracted with ethyl acetate (100 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated. The crude residue was purified by flash column chromatography (about 20 g silica, 10% EtOAc/CH2Cl2 through 15% EtOAc/CH2Cl2) to give the desired product (209 mg, 1.10 mmol, 89%).

1. additionBorane-dimethylsulfide complex (0.9 mL, 1.8 mmol) was added
2. temperaturethe reaction was cooled to −40° C.
3. waitAfter 15 minutes
4. temperaturethe reaction was warmed slowly until the frozen mixture
5. washthe mixture was washed with brine (3×10 mL)
6. extractionThe combined aqueous layers were extracted with ethyl acetate (100 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude residue was purified by flash column chromatography (about 20 g silica, 10% EtOAc/CH2Cl2 through 15% EtOAc/CH2Cl2)

ORD record

ord-616a080aa5104c37834700ef5b56d5d1

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700628B2