1-Benzyl 4-tert-butyl 5,6-dimethyl-1,4-diazepane-1,4-dicarboxylate → Tert-butyl 6,7-dimethyl-1,4-diazepane-1-carboxylate

HRID 1808914Notes

Reaction equation

HRID 1808914 reaction equation
[CH3:1][CH:2]1[CH:8]([CH3:9])[CH2:7][N:6](C(OCC2C=CC=CC=2)=O)[CH2:5][CH2:4][N:3]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[H][H]>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[CH3:9][CH:8]1[CH:2]([CH3:1])[N:3]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:4][CH2:5][NH:6][CH2:7]1

Participants

5

Reactant 2

HCID 684245271-Benzyl 4-tert-butyl 5,6-dimethyl-1,4-diazepane-1,4-dicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 59527658Tert-butyl 6,7-dimethyl-1,4-diazepane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-3 (3.3 g, 9.1 mmol) in ethyl acetate (45 mL) was added 20% palladium hydroxide on carbon (256 mg) and the reaction was stirred at room temperature under balloon pressure of hydrogen gas overnight. The reaction was filtered through celite and concentrated in vacuo to afford 1-4.

Workup

  1. filtrationThe reaction was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customto afford 1-4

Sources & evidence

ORD record
ord-511a89bcc0d640cf9be3f0e9b4c144d8
Source dataset
uspto-grants-2013_01
Patent number
US08362009B2

Reaction notes

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