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

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Reaction Conditions

Reaction Steps

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.

Provenance & Evidence