tert-butyl 5-(4-cyanophenyl)-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate → Tert-butyl 4-(4-cyanophenyl)azepane-1-carboxylate

HRID 541216Notes

Reaction equation

HRID 541216 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:14][CH:15]=2)=[CH:5][CH:4]=1)#[N:2].C(C1C=CC(C2CCCN(C(OC(C)(C)C)=O)CC=2)=CC=1)#N>[Pd].C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 68288828tert-butyl 5-(4-cyanophenyl)-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate2×HCID 68288921tert-butyl 4-(4-cyanophenyl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate

Product 1

HCID 68288974Tert-butyl 4-(4-cyanophenyl)azepane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a 25 mL round bottom flask containing a mixture of tert-butyl 4-(4-cyanophenyl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate and tert-butyl 5-(4-cyanophenyl)-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate (compound 40.2, 167 mg, 0.56 mmol) was added 10% palladium on carbon (40 mg) and ethyl acetate (6 mL). The system was purged with nitrogen then charged with hydrogen and stirred at room temperature. After purging the system with nitrogen, the mixture was filtered through celite and the filtrate was concentrated. The residue was purified by preparative TLC to obtain a colorless wax (77 mg, 45%). m/z (ES+) 245 (M minus t-butyl+H)+.

Workup

  1. additionTo a 25 mL round bottom flask containing
  2. customThe system was purged with nitrogen
  3. additionthen charged with hydrogen
  4. customAfter purging the system with nitrogen
  5. filtrationthe mixture was filtered through celite
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by preparative TLC
  8. customto obtain a colorless wax (77 mg, 45%)

Sources & evidence

ORD record
ord-56a6a30c6025463cae99f8cfdfec9a05
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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