Ammonia chloride → tert-Butyl (3-hydroxycyclohexyl)carbamate

Temperature

-75 °C

To a degassed suspension of tert-butyl(3-oxocyclohexyl)carbamate (4.0 g, 18.78 mmol) in dry THF 200 mL) was added a solution of methyllithium in THF (3M, 25.0 mL, 75 mmol) at −75° C. The resulting reaction mixture was stirred at −75° C. for 1 h. A solution of methyllithium in THF (3M, 25.0 mL, 75 mmol) was added at −75° C. and the mixture was stirred for 1 h. Aqueous ammonia chloride solution was added dropwise to quench the reaction. The resulting reaction mixture was continued to stir at room temperature for 2 h. The reaction mixture was extracted with ethyl acetate (150 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford the crude product (4.0 g, crude), which was used directly in the next step without purification. MS (ESI) m/z 230.1 [M+H]+.

1. customThe resulting reaction mixture
2. stirringthe mixture was stirred for 1 h
3. customto quench
4. customthe reaction
5. customThe resulting reaction mixture
6. stirringto stir at room temperature for 2 h
7. extractionThe reaction mixture was extracted with ethyl acetate (150 mL×3)
8. washThe combined organic layers were washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated under vacuum

ORD record

ord-3ff630cd5d1c4048983635122d7f8d52

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156798B2