(2S)-1-Azido-4,4,4-trifluoro-2-butanol → HCID 34178040, compound
Reaction equation
[N:1]([CH2:4][C@@H:5]([OH:11])[CH2:6][C:7]([F:10])([F:9])[F:8])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@@H:5]([OH:11])[CH2:6][C:7]([F:10])([F:9])[F:8]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The slurry of (S)-1-azido-4,4,4-trifluorobutan-2-ol (2.26 g, 13 mmol) and Pd/C (200 mg) in MeOH (20 mL) was subjected to balloon hydrogenation for 18 hr. The reaction mixture was filtered through a celite pad and the filtrate was concentrated in vacuo to give (S)-1-amino-4,4,4-trifluorobutan-2-ol as a crude product (1.02 g, 45%). NMR: 400 MHz 1H (CDCl3) 3.88 ppm, 1 H, m, J=7.85, 7.85, 3.84, 3.74 Hz; 2.93 ppm, 1 H, dd, J=12.74, 3.52 Hz; 2.61 ppm, 1H, dd, J=12.52, 8.13 Hz; 2.34 ppm, 1 H, m; 2.21 ppm, 1 H, m; 1.91 ppm, 3 H, s.
Workup
- customfor 18 hr
- filtrationThe reaction mixture was filtered through a celite pad
- concentrationthe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-07147358148b446dac8e4e5d3da24c6e
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07888376B2
Reaction notes
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