HCID 13559545, compound → HCID 56624700, compound

HRID 638624Notes

Reaction equation

HRID 638624 reaction equation
[H][H].[CH2:3]([O:10][CH2:11][C@@H:12]1[C@@H:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:15]=[CH:14][C@@H:13]1[OH:22])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>[Pt]=O.C(OCC)C>[CH2:3]([O:10][CH2:11][C@@H:12]1[C@H:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:14][C@H:13]1[OH:22])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 13559545HCID 13559545, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 56624700HCID 56624700, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 3283Diethyl EtherSolvent

Procedure

In an atmosphere of hydrogen, a mixture of 10.0 g of (1S,2S,3S)-2-benzyloxymethyl-3-methoxycarbonylmethyl-4-cyclopenten-1-ol (prepared in Reference Example 1), 60.0 mg of platinum oxide and 50 ml of diethyl ether was stirred for 2.5 hrs at room temperature. The mixture was filtered for removing platinum oxide. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (2:1) as eluent to give 8.55 of the title compound having the following physical characteristics, in a 85% yield.

Workup

  1. filtrationThe mixture was filtered
  2. customfor removing platinum oxide
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using
  5. additiona mixture of cyclohexane and ethyl acetate (2:1) as eluent

Sources & evidence

ORD record
ord-0cc2e9b793e74001bce5f17c6ebdc8da
Source dataset
uspto-grants-1985_12
Patent number
US04562207

Reaction notes

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