Pivaloyl chloride → (2S)-trans-N-[(1S,2S)-2-hydroxycyclohexane-1-yl]-3-butyloxiranecarboxamide

Under ice-cooling, to 20 ml of an anhydrous tetrahydrofuran solution containing 2.3 g (7 mmol) of (2S-trans)-3-butyl-oxirane carboxylic acid.dicyclohexylammonium salt was added 2 ml of an anhydrous tetrahydrofuran solution containing 844 mg (7 mmol) of pivaloyl chloride, and the mixture was stirred at the same temperature for 15 minutes. Moreover, the temperature of the reaction mixture was returned to room temperature and the mixture was further stirred for 2 hours. After removing insoluble material in the reaction mixture by filtration, the filtrate was added to 20 ml of an anhydrous tetrahydrofuran solution containing 806 mg (7 mmol) of (1S,2S)-2-aminocyclohexanol under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. Under reduced pressure, the reaction mixture was concentrated and ethyl acetate was added to the concentrate, and the resulting mixture was washed successively with a 10% aqueous potassium hydrogen sulfate solution, a saturated aqueous sodium hydrogen carbonate solution, and then, a saturated NaCl solution. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 1.69 g (Yield: 100%) of the title compound.

1. customwas returned to room temperature
2. stirringthe mixture was further stirred for 2 hours
3. customAfter removing insoluble material in the reaction mixture
4. filtrationby filtration
5. additionthe filtrate was added to 20 ml of an anhydrous tetrahydrofuran solution
6. temperaturecooling
7. stirringthe resulting mixture was stirred at room temperature for 2 hours
8. concentrationUnder reduced pressure, the reaction mixture was concentrated
9. additionethyl acetate was added to the concentrate
10. washthe resulting mixture was washed successively with a 10% aqueous potassium hydrogen sulfate solution
11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
12. customthe solvent was removed under reduced pressure

ORD record

ord-ca9dda6e15a0485e92bd891aa9e3d56f

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163943B2