1,1-dimethylethyl [(3S)-1-methyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate → (S)-tert-butyl 1-methyl-2-oxoazepan-3-ylcarbamate

HRID 1366609Notes

Reaction equation

HRID 1366609 reaction equation
[CH3:1][N:2]1[CH2:8][CH:7]=[CH:6][CH2:5][C@H:4]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]1=[O:17].[H][H]>CO.[Pd]>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[C:3]1=[O:17]

Participants

5

Reactant 2

HCID 866369401,1-dimethylethyl [(3S)-1-methyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 60110341(S)-tert-butyl 1-methyl-2-oxoazepan-3-ylcarbamateYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a degassed solution of 1,1-dimethylethyl [(3S)-1-methyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl]carbamate (Example 94) (680 mg, 2.8 mmol) in MeOH (20 mL) was added 10% Pd/C (100 mg) and the resulting suspension was stirred overnight under a balloon of hydrogen. Filtration of the catalyst and concentration of the filtrate under reduced pressure yielded 1,1-dimethylethyl [(3S)-1-methyl-2-oxohexahydro-1H-azepin-3-yl]carbamate (470 mg, 88%). LCMS: (M−tBut)+: 186.2.

Workup

  1. filtrationFiltration of the catalyst and concentration of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-517ae9aae11d4d0c979f97fbb835b2f8
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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