3-amino-2,2-dimethylcyclohexan-1-ol

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-hydroxy-2,2-dimethylcyclohexanone oxime (1.8 g, crude) and Raney nickel (1.5 g) in a MeOH (50 mL) and ammonia (5 mL) was stirred at 25° C. under hydrogen atmosphere overnight. The reaction mixture was filtered through celite and the filter cake was rinsed with MeOH (50 mL). The filtrate was concentrated to afford the title compound (1.30 g, crude). MS (ESI) m/z 144.2 [M+H]+. The reaction mixture was filtered through celite the filter cake was rinsed with MeOH (50 mL) The filtrate was concentrated

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-amino-2,2-dimethylcyclohexanol (1.30 g, crude) and 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (1.35 g, 7.27 mmol), and DIEA (1.93 g, 15.0 mmol) in isopropanol (14 mL) was stirred at 90° C. for 1 h. After removal of the solvent, the residue was purified by silica gel column chromatography (10%-30% ethyl acetate in petroleum ether) to afford the title compound (820 mg, 2.81 mmol, 38% yield), which was separated by chiral column (Superchiral S-AD, 0.46 cm I.D.×25 cm L, 5 μl, CO2/MeOH/DEA=80/20/0.05 (v/v/v); Flow: 2.5 ml/min, 254 nm, T=35° C.), then by chiral column: Chiralpak IC, 0.46 cm I.D.×25 cm L, 5 μl, CO2/MeOH/DEA=70/30/0.05 (v/v/v); Flow: 2.5 ml/min, 254 nm, T=35° C.) to give four isomers (peak 1: 90 mg, d.e.=100%, e.e.=100%, peak 2: 220 mg, d.e.=99.7%, e.e.=100%, peak 3: 210 mg, d.e.=100%, e.e.=97.3%, peak 4:125 mg, d.e.=99.6%, e.e.=100%. Peak 1 and peak 4 were determinated to be cis-isomers and peak 2 and peak 3 were determinated to be trans-isomers by 2D-NMR). MS (ESI) m/z 293.1 [M+H]+ After removal of the solvent the residue was purified by silica gel column chromatography (10%-30% ethyl acetate in petroleum ether)

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-hydroxy-2,2-dimethylcyclohexanone oxime (1.8 g, crude) and Raney nickel (1.5 g) in a MeOH (50 mL) and ammonia (5 mL) was stirred at 25° C. under hydrogen atmosphere overnight. The reaction mixture was filtered through celite and the filter cake was rinsed with MeOH (50 mL). The filtrate was concentrated to afford the title compound (1.30 g, crude). MS (ESI) m/z 144.2 [M+H]+. The reaction mixture was filtered through celite the filter cake was rinsed with MeOH (50 mL) The filtrate was concentrated