Aluminium lithium hydride → (2S,3S)-2-amino-3-ethyl-5,5,5-trifluoropentan-1-ol
Reaction equation
[N:1]([C@@H:4]([C@@H:8]([CH2:14][CH3:15])[CH2:9][C:10]([F:13])([F:12])[F:11])[C:5](O)=[O:6])=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:1][C@@H:4]([C@@H:8]([CH2:14][CH3:15])[CH2:9][C:10]([F:11])([F:12])[F:13])[CH2:5][OH:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
(2S,3S)-2-Azido-3-ethyl-5,5,5-trifluoro-pentanoic acid was dissolved in THF (5 mL) at 0° C. and lithium aluminum hydride (1 M solution in THF) (1 mL, 1 mmol) was added. The resulting solution was stirred at 40° C. for 2 h. The reaction was quenched by sequential addition of water (60 μL), 15% aqueous sodium hydroxide (60 μL), and water (150 μL) with vigorous stirring between each addition. The mixture was then filtered and concentrated to give (2S,3S)-2-amino-3-ethyl-5,5,5-trifluoro-pentan-1-ol.