Water → HCID 54464892, compound

HRID 344062Notes

Reaction equation

HRID 344062 reaction equation
[C:1]1([N:7]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:8]([O:10][CH2:11][C:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:13]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)(=[O:37])C.[OH2:41]>C(#N)C>[OH:41][CH:13]1[C:14]2[C:19](=[C:18]([O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:17]=[CH:16][CH:15]=2)[CH2:20][CH2:21][C:12]1([OH:37])[CH2:11][O:10][C:8](=[O:9])[N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 53851475HCID 53851475, compound

Product 1

HCID 54464892HCID 54464892, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(N,N-diphenylcarbamoyloxymethyl)-5-ethoxycarbonylmethyloxy-3,4-dihydronaphthalene (270 mg) in a mixture of acetonitrile (10 ml) and water (5 ml) were added 4-methylmorphorine N-oxide (0.34 ml) and OSO4 (1 ml, 2.5% in t-butyl alcohol) at 0° C. After being stirred for 4 hours, the solution was diluted into ethyl acetate. The mixture was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1,2-dihydroxy-2-(N,N-diphenylcarbamoyloxymethyl)-5-ethoxycarbonylmethyloxy-1,2,3,4-tetrahydronaphthalene.

Workup

  1. washThe mixture was washed with 1N-HCl solution, sat. NaHCO3, and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-95c744b779414688869458a41b28a43a
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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