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With sodium tetrahydroborate In methanol at 0 - 20℃; for 14 h;
Sodium borohydride (710 mg, 18.8 mmol, 2.0 eq.) was added to a solution of tert-butyl 3-oxocyclohexylcarbamate (2.0 g, 9.38 mmol, 1.0 eq.) in methanol (20 mL) at 0° C. The reaction was stirred at room temperature for 14 hours, quenched with water (20 mL) and extracted with ethyl acetate (30 mL*3). The combined organic phases were dried over anhydrous sodium sulfate, and concentrated to give the title compound (2.0 g, yield: 100percent).
81%
With L-Selectride In tetrahydrofuran at -78℃; for 2 h;
Step A - Synthesis of Intermediate Compound 6b To a solution of compound 6a (5.0 g, 23.44 mmol) in THF (50 ml) was added L- Selectride (35.2 mL, 35.2 mmol) at -78°C. The mixture was stirred at -78°C for 2 h. TLC showed the reaction was complete and the reaction was quenched with 10percent aqueous NaOH (20 mL). After concentration, the residue was diluted with EtOAc (200 mL), washed with brine (200 mL), dried over Na2S04, and concentrated in vacuo. The residue was purified using column chromatography (Si02, Petroleum ether: EtOAc = 10: 1 to 1 : 1) to provide compound 6b (4.1 g, 81 percent yield) as a white solid.
C. tert-butyl(3-Hydroxycyclohexyl)carbamate To a solution of 3-aminocyclohexanol (3.0 g, 26.0 mol) in THF (30 mL) was added di-tert-butyl dicarbonate (6.74 g, 31.2 mmol). The resulting mixture was stirred at 50° C. for 16 h. Then the reaction mixture was concentrated in vacuum and purified by silica gel column chromatography (30percent ethyl acetate in petroleum ether) to afford the desired compound (4.40 g, 20.46 mmol, 78percent yield). MS (ESI) m/z 216.1 [M+H]+.
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