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

Participants

Reaction Steps

To a stirred solution of (3RS,4R)-2,2-dimethyl-4-(trityl-amino)-hexan-3-ol (0.57 g, 1 eq, 1.47 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: 0.21 g (100%). (55% de 3S,4R: 45% de 3R,4R). 1H-NMR (d6-DMSO, 250 MHz): δ 0.84-0.99 (m, 3H, NH2CH(CH2CH3)CH(C(CH3)3)OH), 1.25-1.29 (m, 9H, NH2CH(CH2CH3)CH(C(CH3)3)OH), 1.20-1.72 (m, 2H, NH2CH(CH2CH3)CH(C(CH3)3)OH), 3.14 (m, 1H, NH2CH(CH2CH3)CH(C(CH3)3)OH), 3.39 (m, 1H, NH2CH(CH2CH3)CH(C(CH3)3)OH), 3.65 (m, 1H, NH2CH(CH2CH3)CH(C(CH3)3)OH), 7.43, 7.77 & 8.54 (3×bs, 2H, NH2CH(CH2CH3)CH(CH(CH3)2)OH).

Provenance & Evidence