(5RS,6SR)-2,2-dimethyl-6-{[(1S)-1-phenylethyl]amino}-1,3-dioxepan-5-ol → (5S,6R)-6-amino-2,2-dimethyl-1,3-dioxepan-5-ol

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Reaction Conditions

Reaction Steps

To (5S,6R)-2,2-dimethyl-6-((S)-1-phenylethylamino)-1,3-dioxepan-5-ol (500 mg, 1.88 mmol) in iso-propanol (5 ml) was added 10% Pd—C (100 mg). The mixture was stirred at 50° C. under an atmospheric pressure of H2 overnight. Then the solution was filtered on a pad of Celite and the pad washed with MeOH (20 ml). The filtrate was evaporated to dryness to give (5S,6R)-6-amino-2,2-dimethyl-1,3-dioxepan-5-ol (300 mg, 1.86 mmol, 99% yield) as a white solid. 1H NMR (CDCl3) 1.03 (3H, s), 1.06 (3H, s), 2.61 (1H, d, OH), 2.75 (1H, m), 3.38 (1H, m), 3.46 (1H, dd, J 5.3 and 12.5 Hz), 3.57 (1H, dd, J 5.9 and 12.5 Hz), 3.75 (1H, dd, J 2.3 and 12.5 Hz), 3.80 (1H, dd, J 1.8 and 12.5 Hz). 13C NMR (CDCl3) 25.0, 25.1, 56.1, 61.6, 62.8, 74.6, 101.7.

Provenance & Evidence