Ethanol → HCID 67490849, compound

A 1.09 M solution of a borane/tetrahydrofuran complex in tetrahydrofuran (3.6 mL, 3.98 mmol) was added dropwise to a solution of (1S,5S)-1-(tert-butoxycarbonylamino)-5-methyl-4-oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.2.0]heptane (548 mg, 1.59 mmol) in tetrahydrofuran (10 mL) at 0° C. over five minutes. After heating to room temperature and stirring for three hours, a 1.09 M solution of a borane/tetrahydrofuran complex in tetrahydrofuran (3.6 mL, 3.98 mmol) was added at the same temperature. The mixture was stirred at room temperature for 15 hours and then cooled to 0° C. A mixture of ethanol (9.0 mL)-water (1.0 mL) was carefully added dropwise. After addition of triethylamine (3.0 mL) dropwise, the mixture was heated to reflux for one hour. The reaction solution was concentrated, and the precipitated white solid was removed by filtration through Celite. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→5:1) to give 184 mg (35%) of the title compound as a colorless oil.

1. stirringThe mixture was stirred at room temperature for 15 hours
2. temperaturecooled to 0° C
3. additionwas carefully added dropwise
4. temperaturethe mixture was heated
5. temperatureto reflux for one hour
6. concentrationThe reaction solution was concentrated
7. customthe precipitated white solid was removed by filtration through Celite
8. concentrationThe filtrate was concentrated
9. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1→5:1)

ORD record

ord-5248765582fb44409deda2a7e58d91d8

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08618094B2