Methyl iodide → Carbamic acid, N-[(1R,3S)-3-methoxycyclohexyl]-, 1,1-dimethylethyl ester

To a solution of tert-butyl (1R,3S)-3-hydroxycyclohexylcarbamate (1.78 g, 8.27 mmol) in anhydrous THF (8 mL) was added sodium hydride (0.230 g, 9.09 mmol) in portions under nitrogen at 0° C. The mixture was warmed to room temperature and stirred for 30 min. A solution of iodomethane (0.824 mL, 13.23 mmol) in anhydrous THF (4 mL) was added drop wise to the mixture at 0° C. and the resulting mixture was stirred at room temperature for 20 h. The crude mixture was quenched with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo, and then purified by silica gel chromatography (0-50% ethyl acetate in hexanes). The product fractions were combined and concentrated to afford tert-butyl (1R,3S)-3-methoxycyclohexylcarbamate (1.0686 g, 4.66 mmol, 56.4% yield) as a white solid; MS (ESI) m/z 230.5 [M+1]+.

1. stirringthe resulting mixture was stirred at room temperature for 20 h
2. customThe crude mixture was quenched with water (50 mL)
3. extractionextracted with ethyl acetate (3×50 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated in vacuo
8. custompurified by silica gel chromatography (0-50% ethyl acetate in hexanes)
9. concentrationconcentrated

ORD record

ord-fe1816472acd4fa8ab54d7c5d55df8ab

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139534B2