Trifluoroacetic acid → (3RS,4S)-4-amino-2,2-dimethyl-hexan-3-ol

Participants

Reaction Steps

To a stirred solution of (3RS,4S)-2,2-dimethyl-4-(trityl-amino)-hexan-3-ol (0.47 g, 1 eq, 1.21 mmol) in DCM (10 mL) under an argon atmosphere at room temperature, was added CF3COOH (5 mL) dropwise, and the solution was stirred at this temperature for 1 h. The solvent was evaporated in vacuo, the residue was precipitated from Et2O (3 mL) with hexane (20 mL) with stirring to give a yellow oil. The solvent was decanted from the oil, and the oil was washed with hexane (20 mL) and dried in vacuo to afford the title compound as a light yellow oil. Yield: 0.18 g (99%). (53% de 3R,4S: 47% de 3S,4S). 1H-NMR (d6-DMSO, 250 MHz): δ 0.86-0.99 (m, 3H, NH2CH(CH2CH3)CH(C(CH3)3)OH), 1.25-1.30 (m, 9H, NH2CH(CH2CH3)CH(C(CH3)3)OH), 1.20-1.67 (m, 2H, NH2CH(CH2CH3)CH(C(CH3)3)OH), 3.14 (m, 1H, NH2CH(CH2CH3)CH(C(CH3)3)OH), 3.38 (m, 1H, NH2CH(CH2CH3)CH(C(CH3)3)OH), 3.64 (m, 1H, NH2CH(CH2CH3)CH(C(CH3)3)OH), 7.41, 7.73 & 8.44 (3×bs, 2H, NH2CH(CH2CH3)CH(CH(CH3)2)OH).

Provenance & Evidence