Pyridine → HCID 23093564, compound

To a mixture of tert-butyl 2-hydroxyethyl(methyl)carbamate (1.75 g) obtained in Reference Synthetic 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 added thereto. After stirring at room temperature for 2 hrs, pyridine (0.65 mL) and cyclohexanecarbonyl chloride (0.58 mL) was further added, and stirred overnight at room temperature. To the reaction solution was added ethyl acetate (50 mL), and washed sequentially with water (50 mL), 5% aqueous solution of citric acid (50 mL) and saturated saline (50 mL), and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and to the residue was added 4N hydrogen chloride-ethyl acetate solution (10 mL). After stirring at room temperature for 2 hrs, diethyl ether (10 mL) was added thereto, and the depositting solid was collected by filtration. The solid was dried under reduced pressure to give title compound as white solid (1.88 g).

1. additionwas added
2. stirringstirred overnight at room temperature
3. washwashed sequentially with water (50 mL), 5% aqueous solution of citric acid (50 mL) and saturated saline (50 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationThe solution was concentrated under reduced pressure
6. additionto the residue was added 4N hydrogen chloride-ethyl acetate solution (10 mL)
7. stirringAfter stirring at room temperature for 2 hrs
8. additiondiethyl ether (10 mL) was added
9. filtrationthe depositting solid was collected by filtration
10. customThe solid was dried under reduced pressure

ORD record

ord-8e1dce560f7b4e059025f6c3e7d43a8f

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08449911B2