Aluminium lithium hydride → 1-Pentanol, 2-amino-3-ethyl-5,5,5-trifluoro-, (2S,3S)-

Temperature

25 °C

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)−.

1. customThe reaction was quenched by sequential addition of H2O (0.3 mL), 1N NaOH (0.9 mL) and H2O (0.3 mL) at 0° C
2. customThe precipitate that formed after 5 h
3. filtrationwas filtered off
4. dry with materialThe mother liquor was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-52a4dfa17fb84d13bed706fc43e8a75b

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547725B2