cis-4-(aminomethyl)cyclohexan-1-ol synthesis

Yield:874823-57-1 93.2%

Reaction Conditions:

with ammonia;hydrogen;nickel in methanol; under 2327.23 Torr;

Steps:

50

N-methyl-N-[1-(trans-4-{[(5-nitro-2-{[2-(trifluoromethoxy)benzyl]amino}pyrimidin-4-yl)amino]methyl}cyclohexyl)pyrrolidin-3-yl]acetamide cis-4-Hydroxy-cyclohexanecarbonitrile was made according to literature procedures (Noyce, D. S. et al.; J. Org. Chem. 1969; 34, 1247). To a 2 N solution of NH₃ in MeOH (40 mL) in a high pressure autoclave was added cis-4-hydroxy-cyclohexanecarbonitrile (6.6 g, 52.7 mmol) and Raney Ni (1.0 g, 17 mmol, 0.3 equiv.) The mixture was placed under 45 psi H₂ and shaken overnight. The pressure was released and the reaction filtered through a pad of Celite. The filter pad was washed with EtOAc and the mixture was concentrated under reduced pressure to provide a yellow oil as cis-4-aminomethyl-cyclohexanol (6.3 5g, 49.1 mmol, 93.2%).

References:

US2006/25433,2006,A1 Location in patent:Page/Page column 133