Triethylamine → Carbamic acid, [(1S,2R)-2-(hydroxymethyl)cyclohexyl]-, 1,1-dimethylethyl ester

racemic-1,1-Dimethylethyl [(1S,2R)-2-(hydroxymethyl)cyclohexyl]carbamate racemic-[(1R,2S,5S)-2-Amino-5-phenylcyclohexyl]methanol hydrochloride (800 mg, 4.82 mmol) was dissolved in MeOH (40 mL) and bis(1,1-dimethylethyl) dicarbonate (1.16 g, 5.30 mmol) and triethylamine (4 mL, 28.92 mmol) were added and the mixture was stirred 18 hours at ambient temperature. The solvents were removed tinder reduced pressure, ethyl acetate and aqueous saturated sodium bicarbonate were added and the product was extracted with ethyl acetate. The combined organics were dried over sodium sulfate and the solvents were removed under reduced pressure. Purification by silica gel chromatography (9:1 hexanes:ethyl acetate to ethyl acetate gradient elution) gave 1,1-dimethylethyl racemic-[(1S,2R)-2-(hydroxymethyl)cyclohexyl]carbamate (934 mg, 85%) as a white solid. 1H NMR (CDCl3) δ 4.87 (m, 1H), 4.03-3.95 (m, 2H), 3.26 (m, 1H), 3.15 (m, 1H), 1.73-1.48 (m, 5H), 1.38 (s, 9H), 1.27-1.15 (m, 3H), 0.887 (m, 1H).

1. customThe solvents were removed tinder reduced pressure, ethyl acetate and aqueous saturated sodium bicarbonate
2. additionwere added
3. extractionthe product was extracted with ethyl acetate
4. dry with materialThe combined organics were dried over sodium sulfate
5. customthe solvents were removed under reduced pressure
6. customPurification
7. washby silica gel chromatography (9:1 hexanes:ethyl acetate to ethyl acetate gradient elution)

ORD record

ord-ed49b8fa6f0c48148da24bfcf6ee2ef8

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051337B2