HCID 59485650, compound → HCID 28168138, compound

HRID 1972208Notes

Reaction equation

HRID 1972208 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[NH:5][C@@H:6]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=1)[CH2:7][N:8]=[N+]=[N-])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:21])[NH:5][C@@H:6]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:18])[F:20])[CH:12]=1)[CH2:7][NH2:8])[CH3:2]

Participants

4

Reactant 1

HCID 59485650HCID 59485650, compound

Product 1

HCID 28168138HCID 28168138, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (S)-[2-azido-1-(3-trifluoromethyl-phenyl)-ethyl]-carbamic acid ethyl ester (4.60 g, 15.2 mmol) in EtOH (200 mL) is added 10% Pd/C (˜200 mg). The resulted mixture is then degassed and filled with H2 and stirred at room temperature under H2 for 14 h. The mixture is then filtered through a pat of Celite to remove the Pd/C and washed with EtOH (3×10 mL). The filtrate is concentrate to provide the crude (S)-[2-amino-1-(3-trifluoromethyl-phenyl)-ethyl]-carbamic acid ethyl ester (˜4.0 g, 95%), which is used for next step without further purification.

Workup

  1. customThe resulted mixture is then degassed
  2. additionfilled with H2
  3. filtrationThe mixture is then filtered through a pat of Celite
  4. customto remove the Pd/C
  5. washwashed with EtOH (3×10 mL)
  6. concentrationThe filtrate is concentrate

Sources & evidence

ORD record
ord-7a34ce30c6104e39a987b8a21ab86f4c
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

Loading…