(Z)-tert-butyl 4,4-dimethyl-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate → Tert-butyl 4,4-dimethyl-2-oxo-1-phenylazepan-3-ylcarbamate

HRID 529478Notes

Reaction equation

HRID 529478 reaction equation
[CH3:1][C:2]1([CH3:24])[CH:3]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:4](=[O:15])[N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH:7]=[CH:8]1.[H][H]>[Pd].CCOC(C)=O>[CH3:1][C:2]1([CH3:24])[CH2:8][CH2:7][CH2:6][N:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4](=[O:15])[CH:3]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 68292253(Z)-tert-butyl 4,4-dimethyl-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 68292213Tert-butyl 4,4-dimethyl-2-oxo-1-phenylazepan-3-ylcarbamateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a 2-neck round bottom flask was added (Z)-tert-butyl 4,4-dimethyl-2-oxo-1-phenyl-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate (7 mg, 0.02 mmol), 10% Pd/C (2.3 mg, 0.021 mmol) and EtOAc (1 mL). The reaction was then charged with hydrogen with a balloon and then stirred at rt for 2 hr. The reaction was filtered through CELITE® and the filtrate was concentrated to give tert-butyl 4,4-dimethyl-2-oxo-1-phenylazepan-3-ylcarbamate (6.5 mg, 0.020 mmol, 92% yield) as a clear film. Anal. Calcd. for C19H28N2O3 m/z 332.2. found: 333.2 (M+H)+.

Workup

  1. filtrationThe reaction was filtered through CELITE®
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-72093bb819b14fad9f9718c923643310
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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