Tert-butyl trans-4-azido-3-fluoro-piperidine-1-carboxylate → tert-Butyl (3S,4S)-4-amino-3-fluoropiperidine-1-carboxylate

HRID 588485Notes

Reaction equation

HRID 588485 reaction equation
[N:1]([C@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][C@@H:5]1[F:17])=[N+]=[N-]>[Pd].CCO>[NH2:1][C@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:6][C@@H:5]1[F:17]

Participants

4

Reactant 1

HCID 58073560Tert-butyl trans-4-azido-3-fluoro-piperidine-1-carboxylate

Product 1

HCID 57415840tert-Butyl (3S,4S)-4-amino-3-fluoropiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon 10% (0.1 g) was added to a solution of tert-butyl (3S,4S)-4-azido-3-fluoropiperidine-1-carboxylate, 4.4 (0.4 g, 0.00163 mol) dissolved in EtOH (60 mL). The reaction was placed under a hydrogen atmosphere (40 psi pressure) for 16 h. The mixture was filtered through celite-bed and concentrated under reduced pressure to obtain the title compound tert-butyl (3S,4S)-4-amino-3-fluoropiperidine-1-carboxylate, 4.6 (0.4 g crude).

Workup

  1. customfor 16 h
  2. filtrationThe mixture was filtered through celite-bed and
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a5e29f6b8dd14ddeb345292c8ef07d79
Source dataset
uspto-grants-2016_01
Patent number
US09227969B2

Reaction notes

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