Water → HCID 54464892, compound

HRID 963732Notes

Reaction equation

HRID 963732 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.O=[Os](=O)(=O)=O>[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

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 53851475HCID 53851475, compound

Product 1

HCID 54464892HCID 54464892, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 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
  2. dry with materialHCl solution, sat. NaHCO3, and brine, dried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-20127e4fc4d04843835d133de636a287
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

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