(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

HRID 533210Notes

Reaction equation

[CH3:1][C:2]1([CH3:19])[O:8][CH2:7][C@@H:6]([OH:9])[C@H:5]([NH:10][C@H](C2C=CC=CC=2)C)[CH2:4][O:3]1>C(O)(C)C.[Pd]>[NH2:10][C@@H:5]1[CH2:4][O:3][C:2]([CH3:1])([CH3:19])[O:8][CH2:7][C@H:6]1[OH:9]

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

filtrationThen the solution was filtered on a pad of Celite
washthe pad washed with MeOH (20 ml)
customThe filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-b06e7b5ad7d44246afac86b6d74725d8
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853224B2

Reaction notes

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