4,4,4-Trifluorovaline → 2-Amino-4,4,4-trifluoro-3-methylbutan-1-ol

To a chilled (00° C.) solution of 2-amino-4,4,4-trifluoro-3-methylbutanoic acid (736 mg, 4.30 mmol) in THF (9 mL) was added aluminum (111) lithium hydride (2.26 mL, 9.03 mmol, 4M) dropwise. After addition complete, the reaction was allowed to stir at ambient temperature for 1 hour. Cool to 0° C. and quench w/sat. Na2SO4 soln, added EtOAc (50 mL), Na2SO4, filtered, conc. in vacuo afforded material that was a mixture of the title compound and the starting material acid in a 3:2 ratio which was used crude in the next step. 1H NMR (400 MHz, CDCl3) δ 3.71 (dd, J=10.7, 3.7 Hz, 1H), 3.57 (dd, J=10.4, 5.2 Hz, 1H), 3.45 (ddd, J=10.7, 8.0, 4.8 Hz, 2H), 3.28 (ddd, J=8.2, 5.3, 2.9 Hz, 1H), 3.06 (td, J=7.3, 3.6 Hz, 1H), 2.44-2.20 (m, 2H), 2.04-1.54 (m, 1H), 1.21-1.08 (m, 7H). 19F NMR (376 MHz, CDCl3) δ−68.33 (s), −70.12 (s).

1. additionAfter addition complete
2. temperatureCool to 0° C.
3. customquench
4. additionNa2SO4 soln, added EtOAc (50 mL), Na2SO4
5. filtrationfiltered, conc. in vacuo
6. customafforded material that

ORD 기록

ord-0308faff7ca4409aabf50c68522aeb07

출처 데이터셋

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09434719B2