Pyridine → HCID 66955715, compound

Methyl chloroformate (0.468 mL, 6.06 mmol) was added dropwise, over a period of 20 min, under argon atmosphere, at 0° C., to a mixture of (4-amino-cyclohexyl)-carbamic acid tert-butyl ester (1.0 g, 4.67 mmol) and pyridine (0.479 mL, 6.06 mmol) in THF (6 mL) and the resulting mixture was stirred at RT for 24 h. The reaction mixture was then evaporated under reduced pressure and water (300 mL) was added to the solid residue. The resulting mixture was extracted 3 times with EtOAc (100 mL), the combined organics were washed 3 times with water (100 mL), twice with NaHSO4 (aq 1%, 150 mL) and twice with water (150 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The remaining white solid was mixed with HCl (2.0 M in MeOH, 200 mL) and the resulting mixture was stirred at RT for 5 h. The reaction mixture was then evaporated under reduced pressure to give 1.1 g of (4-amino-cyclohexyl)-carbamic acid methyl ester hydrochloride salt.

1. customThe reaction mixture was then evaporated under reduced pressure and water (300 mL)
2. additionwas added to the solid residue
3. extractionThe resulting mixture was extracted 3 times with EtOAc (100 mL)
4. washthe combined organics were washed 3 times with water (100 mL)
5. dry with materialtwice with NaHSO4 (aq 1%, 150 mL) and twice with water (150 mL), dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. additionThe remaining white solid was mixed with HCl (2.0 M in MeOH, 200 mL)
9. stirringthe resulting mixture was stirred at RT for 5 h
10. customThe reaction mixture was then evaporated under reduced pressure

ORD record

ord-2e543b7f386540208b7aff2f6e2a9741

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268840B2