(S)-tert-Butyl 5-azido-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate → (S)-tert-Butyl 5-amino-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carboxylate

HRID 507031Notes

Reaction equation

HRID 507031 reaction equation
[N:1]([C@H:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]2[CH:18]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:20]([CH3:22])=[CH:21][C:5]1=2)=[N+]=[N-].[H][H]>[Pd].CO>[NH2:1][C@H:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]2[CH:18]=[C:19]([C:23]([F:26])([F:24])[F:25])[C:20]([CH3:22])=[CH:21][C:5]1=2

Participants

5

Reactant 2

HCID 59432320(S)-tert-Butyl 5-azido-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 59432516(S)-tert-Butyl 5-amino-7-methyl-8-(trifluoromethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Shake a mixture of (S)-tert-butyl 5-azido-7-methyl-8-trifluoromethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (1.44 g, 3.89 mmol) and 5% palladium on charcoal (0.15 g, 50% wet) in methanol (50 mL) under 20 psi of hydrogen in a Parr bottle at room temperature for 12 h. Filter the mixture through Celite® and remove the solvents under reduced pressure to provide the title compound as a colorless oil (1.30 g, >99%), which is used in the next step without further purification. APCI MS m/z 344 (M+H)+.

Workup

  1. filtrationFilter the mixture through Celite®
  2. customremove the solvents under reduced pressure

Sources & evidence

ORD record
ord-48ff4cdda9b54968bc26afe15d815b7c
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

Loading…