Pyridine → HCID 23093564, compound

To a mixture of tert-butyl 2-hydroxyethyl (methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (20 mL) were added pyridine (0.97 mL), and 4-dimethylaminopyridine (catalytic amount), and cyclohexanecarbonyl chloride (1.60 mL) was dropwise added. After stirring at room temperature for 2 hrs., pyridine (0.65 mL) and cyclohexanecarbonyl chloride (0.58 mL) were added, and the mixture was stirred overnight at room temperature. Ethyl acetate (50 mL) was added to the reaction mixture, and the mixture was washed with water (50 mL), a 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, a 4N hydrogen chloride-ethyl acetate solution (10 mL) was added to the residue. After stirring at room temperature for 2 hrs., diethyl ether (10 mL) was added, and the precipitated solid was collected by filtration. The solid was dried under reduced pressure to give the title compound (1.88 g) as a white solid. 1H-NMR (DMSO-d6): 1.10-1.45 (5H, m), 1.54-1.73 (3H, m), 1.83-1.93 (2H, m), 2.29-2.42 (1H, m), 2.54 (3H, s), 3.12-3.18 (2H, m), 4.23-4.29 (2H, m), 9.23 (2H, br).

1. additionwas dropwise added
2. stirringthe mixture was stirred overnight at room temperature
3. washthe mixture was washed with water (50 mL)
4. dry with materiala 5% aqueous citric acid solution (50 mL) and saturated brine (50 mL), and dried over anhydrous magnesium sulfate
5. concentrationAfter concentration under reduced pressure
6. additiona 4N hydrogen chloride-ethyl acetate solution (10 mL) was added to the residue
7. stirringAfter stirring at room temperature for 2 hrs
8. addition, diethyl ether (10 mL) was added
9. filtrationthe precipitated solid was collected by filtration
10. customThe solid was dried under reduced pressure

ORD record

ord-83936aacf984409aa0be605c42d8b031

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08784885B2