[1-(2,4-dimethoxy-benzyl)-4,4-dimethyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl]-carbamic acid tert-butyl ester → HCID 69491024, compound

HRID 852014Notes

Reaction equation

HRID 852014 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]1[C:14]([CH3:16])([CH3:15])[CH:13]=[CH:12][CH2:11][N:10]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=2[O:26][CH3:27])[C:9]1=[O:28])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]1[C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][CH2:11][N:10]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=2[O:26][CH3:27])[C:9]1=[O:28])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 69492432[1-(2,4-dimethoxy-benzyl)-4,4-dimethyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 69491024HCID 69491024, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

[1-(2,4-Dimethoxy-benzyl)-4,4-dimethyl-2-oxo-2,3,4,7-tetrahydro-1H-azepin-3-yl]-carbamic acid tert-butyl ester (260 mg, 0.64 mmol) was dissolved in methanol (10 ml). Palladium on charcoal (30 mg, 10%) was added and the mixture was hydrogenated at room temperature for 90 minutes. The catalyst was filtered off and the filtrate was evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate=1:1) to yield 220 mg (84%) of [1-(2,4-dimethoxy-benzyl)-4,4-dimethyl-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester as a colourless oil; MS: m/e=407.4 (MH+).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by flash chromatography (heptane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-8813226ffd2e4d3e82ca942c7350cfed
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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