((1S,2S)-2-((S)-1-phenylethylamino)cyclohexyl)methanol → [(1S,2S)-2-aminocyclohexyl]methanol

Temperature

60 °C

5% Palladium on carbon (0.05 g) was added to a solution of (1S,2S)-2-[(S)-1-phenylethyl amino]cyclohexyl)methanol (11, 0.5 g, 0.002 mol) dissolved in methanol (15 mL). The mixture was heated at 60° C. under hydrogen (14.5 psi) atmosphere for NLT 3 h. The mixture was cooled to room temperature, flushed with nitrogen, the catalyst was filtered and washed with fresh methanol (10 mL). The combined filtrate was concentrated under vacuum to afford 0.28 g of ((1S,2S)-2-aminocyclohexyl)methanol (17) in quantitative yield as a white solid. [α]23D 9.1 (c, 0.0107 CHCl3), 1H NMR (CDCl3, 400 MHz): δ 3.61-3.54 (m, 2 H), 2.71 (bs, 3H), 2.45 (dt, 1H, J=10.6, 1.2 Hz), 1.85-1.78 (m, 1H), 1.74-1.65 (m, 1H), 1.62-1.53 (m, 1H), 1.40-1.30 (m, 1H), 1.25-1.06 (m, 3H), 0.91-0.80 (m, 1H), 13C NMR (CDCl3): δ 70.2, 57.4, 45.5, 40.1, 28.6, 25.5, 25.5, For NMR of its enantiomer, ((1R,2R)-2-Aminocyclohexyl)methanol, see reference J. Am. Chem. Soc. 1996, 118, 5502.

1. temperatureThe mixture was cooled to room temperature
2. customflushed with nitrogen
3. filtrationthe catalyst was filtered
4. washwashed with fresh methanol (10 mL)
5. concentrationThe combined filtrate was concentrated under vacuum

ORD record

ord-09c14c361118403895db625493221adc

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288565B2