((1S,3S)-3-aminocyclohexyl)methanol synthesis

Yield:-

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethanol at 20; under 2585.81 Torr; for 4 h;

Steps:

83

Preparation 83 [(ISjSSJ-S-Aminocyclohexyllmethanol Benzyl [(1S,3S)-3-(hydroxymethyl)cyclohexyl]carbamate (Preparation 82, 5.7Og, 22.0 mmol) was dissolved in ethanol (70 mL) and the resulting solution was hydrogenated over 10% palladium on carbon (0.57 g) at room temperature and 50 p.s.i pressure for 4 hours. The catalyst was filtered through Celite and the filter pad was washed with ethanol. The filtrate was concentrated to give the title compound as a clear oil (3.0 g). After cooling in the refrigerator overnight a sticky solid was formed. This was dissolved in ethanol (50 mL) and ethyl acetate (100 mL) was added. The resulting clear solution was concentrated to give an oil. Further ethyl acetate (100 mL) was added, the solution was re-evaporated and this process was repeated until the title compound solidified (2.8 g). LCMS: [M+1] 130 (obs) [M+1] 130.20 (calc), RT 0.13 min 100% area.

References:

WO2009/153720,2009,A1 Location in patent:Page/Page column 247