Trifluoroacetic acid → (3RS,4S)-4-Amino-2-methyl-hexan-3-ol

To a stirred solution of (3RS,4S)-2-methyl-4-(trityl-amino)-hexan-3-ol (0.36 g, 1 eq, 0.97 mmol) in DCM (20 mL) under an argon atmosphere at room temperature, was added trifluoroacetic acid (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 ether (10 mL) with hexane (90 mL) with string 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: 0.13 g (100%). (50% de 3R,4S: 50% de 3S,4S), 1H-NMR (d6-DMSO, 250 MHz): δ 0.85-1.01 (m, 9H, NH2CH(CH2CH3)CH(CH(CH3)2)OH), 1.44-1.76 (m, 2H, NH2CH(CH2CH3)CH(CH(CH3)2)OH), 2.94 (m, 1H, NH2CH(CH2CH3)CH(CH(CH3)2)OH), 3.17 (m, 1H, NH2CH(CH2CH3)CH(CH(CH3)2)OH), 3.40 (m, 1H, NH2CH(CH2CH3)CH(CH(CH3)2)OH), 7.54 (bs, 2H, NH2CH(CH2CH3)CH(CH(CH3)2)OH).

1. customThe solvent was evaporated in vacuo
2. customthe residue was precipitated from ether (10 mL) with hexane (90 mL) with string
3. customto give a yellow oil
4. customThe solvent was decanted from the oil
5. washthe oil was washed with hexane (20 mL)
6. customdried in vacuo

ORD-Eintrag

ord-81cc2243cbae4a61aeca5490575d70de

Quelldatensatz

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07612079B2