Reaktion #85617

Reaktionsgleichung

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

aluminum

→

title compound

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter addition complete
2. 2
   TemperaturCool to 0° C.
3. 3
   Sonstigequench
4. 4
   workup.ADDITIONNa2SO4 soln, added EtOAc (50 mL), Na2SO4
5. 5
   Filtrationfiltered, conc. in vacuo
6. 6
   Sonstigeafforded material that

Vorschrift

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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