Ethanol → HCID 53666238, compound

HRID 1976155Notes

Reaction equation

HRID 1976155 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[CH2:4]P(=O)(OC)OC.[H-].[Na+].C(O)C.[C:20]([O:24][C:25]([N:27]1[CH2:33][CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>C1COCC1>[C:20]([O:24][C:25]([N:27]1[CH2:33][CH2:32][CH2:31][C:30](=[CH:4][C:3]2[CH:11]=[CH:12][CH:13]=[CH:14][C:2]=2[Br:1])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 1512679N-Boc-hexahydro-1H-azepin-4-oneHCID 13729876HCID 13729876, compound

Product 1

HCID 53666238HCID 53666238, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of dimethyl 2-bromobenzylphosphonate (5.5 g, 18.7 mmol) in THF was added slowly to a mixture of NaH (0.8 g of a 60% mineral oil dispersion, 20 mmol) in THF (75 ml) and ethanol (0.5 ml) and the mixture was stirred for 45 min. A solution of 1-(tert-butyloxycarbonyl)-hexahydro-4 H-azepin-4-one (3.98 g, 18.7 mmol) in THF was added dropwise and the mixture was heated to reflux for 5 hr. The mixture was cooled and quenched with water. The mixture was diluted with ethyl acetate, washed with water, and dried with brine. The organic layer was concentrated in vacuo. The residue was purified by chromatography on silica gel using 5% ethyl acetate/hexane to give 1-(tert-butoxycarbonyl)-4-[(2-bromophenyl)methylene]-hexahydro4 H-azepine as a clear oil that solidified upon standing (4.3 g, 62.8%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hr
  3. temperatureThe mixture was cooled
  4. customquenched with water
  5. additionThe mixture was diluted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried with brine
  8. concentrationThe organic layer was concentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel using 5% ethyl acetate/hexane

Sources & evidence

ORD record
ord-2f05235c241e4dcba2ee5385e051df2a
Source dataset
uspto-grants-2001_05
Patent number
US06225324B1

Reaction notes

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