HCID 86758060, compound → HCID 9891631, compound

HRID 1934567Notes

Reaction equation

HRID 1934567 reaction equation
[C:1]1([N:7]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:8]([O:10][CH2:11][CH:12]2[CH2:18][CH2:17][CH2:16][C:15]3[C:19]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:21]=[CH:22][C:14]=3[CH:13]2[OH:30])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[C:1]1([N:7]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:8]([O:10][CH2:11][CH:12]2[CH2:18][CH2:17][CH2:16][C:15]3[C:19]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:21]=[CH:22][C:14]=3[C:13]2=[O:30])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 86758060HCID 86758060, compound

Product 1

HCID 9891631HCID 9891631, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst3×HCID 6212ChloroformSolvent

Procedure

To a solution of ethyl {[(5RS,6RS)-6-(N,N -diphenylcarbamoyloxy)methyl-5-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten- 1-yl]oxy}acetate (179 mg) in CHCl3 (15 ml) was added activated MnO2 (636 mg). The mixture was refluxed for 30 minutes. Then after addition of activated MnO2 (636 mg), the mixture was refluxed for 1.5 hours. Furthermore, the mixture was added with activated MnO2 (636 mg) and then refluxed for 1 hour. After cooling, the mixture was filtered. The filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 2:1) to give ethyl {[6-(N,N-diphenylcarbamoyloxy) methyl-5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-yl]oxy}acetate (151.1 mg) as an oil.

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. temperaturethe mixture was refluxed for 1.5 hours
  3. temperaturerefluxed for 1 hour
  4. temperatureAfter cooling
  5. filtrationthe mixture was filtered
  6. customThe filtrate was evaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 2:1)

Sources & evidence

ORD record
ord-640b758710ab4b398bc044f26225f9d3
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

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