Aluminium lithium hydride → (2S,3S)-2-amino-3-ethyl-5,5,5-trifluoropentan-1-ol
反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]([C@@H:10]([C@@H:26]([CH2:32][CH3:33])[CH2:27][C:28]([F:31])([F:30])[F:29])[C:11](N1[C@H](CC2C=CC=CC=2)COC1=O)=[O:12])=[N+]=[N-]>C1COCC1>[NH2:7][C@@H:10]([C@@H:26]([CH2:32][CH3:33])[CH2:27][C:28]([F:29])([F:30])[F:31])[CH2:11][OH:12]参加物
4
反応条件
- 温度
- 25 °C
実験手順
To a gray slurry of LAH (100 mg, 2.65 mmol) in THF (3 mL) at −10° C. was added (4R)-3-[(2S,3S)-2-azido-3-ethyl-5,5,5-trifluoropentanoyl]-4-benzyl-1,3-oxazolidin-2-one (300 mg, 0.78 mmol) as a solution in THF (2 mL) dropwise over 5 min. The resulting slurry was allowed to warm to 25° C. for 19 h. The reaction was quenched by sequential addition of H2O (0.3 mL), 1N NaOH (0.9 mL) and H2O (0.3 mL) at 0° C. The precipitate that formed after 5 h was filtered off. The mother liquor was dried over MgSO4, filtered and concentrated to obtain (2S,3S)-2-amino-3-ethyl-5,5,5-trifluoropentan-1-ol as a light yellow oil (145 mg, 98%). Mass Spectrum (−ESI): 184 (M−H)−.