반응 #85617

반응 방정식

2-amino-4,4,4-trifluoro-3-methylbutanoic acid

aluminum

→

title compound

2-amino-4,4,4-trifluoro-3-methylbutan-1-ol

용매

THF

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition complete
2. 2
   온도Cool to 0° C.
3. 3
   기타quench
4. 4
   workup.ADDITIONNa2SO4 soln, added EtOAc (50 mL), Na2SO4
5. 5
   여과filtered, conc. in vacuo
6. 6
   기타afforded material that

실험 절차

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).

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