Water → 4-Amino-2-hydroxy-1,1,1-trifluorobutane
Reaction equation
[F:1][C:2]([F:10])([F:9])[CH:3]([OH:8])[CH2:4][C:5]([NH2:7])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[NH2:7][CH2:5][CH2:4][CH:3]([OH:8])[C:2]([F:10])([F:9])[F:1]Participants
6
Procedure
To a cooled solution of 4,4,4-trifluoro-3-hydroxybutanamide (2.84 g, 18.1 mmol) in THF (60 mL) was added LiAlH4 (2.063 g, 54.3 mmol) in batches at 0° C. in an ice-water bath. The reaction mixture was then stirred at room temperature for 4 hours under nitrogen atmosphere. After the reaction was completed, 3.3 mL of water, 3.3 mL of 10% NaOH solution and 9.8 mL of water was added into the solution successively at 0° C. The resulting mixture was then filtered through celite, and the filtrate was concentrated in vacuo to afford 4-amino-1,1,1-trifluorobutan-2-ol (2.06 g, yield: 79.6%).
Workup
- filtrationThe resulting mixture was then filtered through celite
- concentrationthe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-402845922c0946dbb0a3fd9ee51ed2c4
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206191B2
Reaction notes
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