Dimethyl Sulfoxide → tert-butyl N-(4-oxocyclohexyl)carbamate

Temperature

-60 °C

To a stirred solution of oxalyl chloride (0.83 g) in dry dichloromethane (15 mL) at -60° C. was added dimethylsulfoxide (1.0 mL) in dichloromethane (3 mL) dropwise. The reaction mixture was stirred at -60° C. for 10 min, then N-tert-butyloxycarbonyl-trans-4-aminocyclohexanol (1.28 g) in dichloromethane (70 mL) was added over 15 min. The resulting mixture was stirred at -60° C. for a further 15 min, then triethylamine (4.2 mL) was added and the solution was allowed to warm to room temperature. The mixture was washed with water (20 mL) and this aqueous layer was extracted once with dichloromethane (20 mL). The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure. Drying under vacuum gave N-tert-butyloxycarbonyl-4-aminocyclohexanone (1.25 g) as a colorless solid.

1. stirringThe resulting mixture was stirred at -60° C. for a further 15 min
2. temperatureto warm to room temperature
3. washThe mixture was washed with water (20 mL)
4. extractionthis aqueous layer was extracted once with dichloromethane (20 mL)
5. dry with materialThe combined organic extracts were dried over MgSO4
6. concentrationconcentrated under reduced pressure
7. customDrying under vacuum

ORD record

ord-4bbfb210e4144643afae0532f7676ce4

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05574044