(S,Z)-tert-butyl 1-(2-methoxyphenyl)-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate → (S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamate

HRID 529533Notes

Reaction equation

HRID 529533 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:15][CH:14]=[CH:13][CH2:12][C@H:11]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]1=[O:24]>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[C:10]1=[O:24]

Participants

4

Reactant 1

HCID 68293065(S,Z)-tert-butyl 1-(2-methoxyphenyl)-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate

Product 1

HCID 68310539(S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamateYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (S,Z)-tert-butyl 1-(2-methoxyphenyl)-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-ylcarbamate (30 mg, 0.090 mmol) in EtOAc (2 mL) was purged with argon for 5 min. Then, 5% Pd/C (25 mg, 0.24 mmol) was added. The reaction mixture was stirred under a hydrogen balloon for 2 hr. The reaction mixture was filtered and the filtrate was concentrated to afford (S)-tert-butyl 1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamate (28 mg, 0.084 mmol, 93% yield) as a foam. Anal. Calcd. for C18H26N2O4 m/z 334.4. found: 335.1 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5e7740e7a8744ac4b9a5cc640cf7fd98
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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