(2S)-1-Azido-4,4,4-trifluoro-2-butanol → HCID 34178040, compound

HRID 1365543Notes

Reaction equation

HRID 1365543 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

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

  1. customfor 18 hr
  2. filtrationThe reaction mixture was filtered through a celite pad
  3. 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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