HCID 131733581, compound → HCID 131733583, compound

To a solution of (R)-tert-butyl (3,3-dimethyl-4-oxocyclohexyl)carbamate (550 mg, 2.28 mmol) in diethyl ether (15 mL) was added methyl magnesium bromide (3 M, 3.00 mL) at −30° C. to −40° C. under nitrogen. The mixture was stirred at this temperature for 0.5 h and quenched with saturated aqueous ammonium chloride solution (150 mL). The aqueous layer was extracted with ethyl acetate (300 mL×3). The combined organic layers were washed with brine (150 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure. The residue was purified silica gel chromatography column (12% ethyl acetate in petroleum ether) to afford the title compound as a yellow oil (520 mg, 5.02 mmol, 88% yield). MS (ESI) m/z 258.2 [M+H]+.

1. customquenched with saturated aqueous ammonium chloride solution (150 mL)
2. extractionThe aqueous layer was extracted with ethyl acetate (300 mL×3)
3. washThe combined organic layers were washed with brine (150 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customThe filtrate was evaporated under reduced pressure
7. customThe residue was purified silica gel chromatography column (12% ethyl acetate in petroleum ether)

ORD record

ord-cc94b880ff6245299f24950109b09764

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156798B2