Wrypvzdhvrcrog-xjksgupxsa- → (2S,3R,5R)-2-methyl-6-oxotetrahydro-2H-pyran-3,5-diyl dibenzoate

HRID 2104226Notes

Reaction equation

HRID 2104226 reaction equation
[C:1]([O:9][C:10]1[C:11]([O:13][C@@H:14]([CH3:26])[C@H:15]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=1)=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CCOC(C)=O.[Pd]>[C:1]([O:9][C@@H:10]1[CH2:16][C@@H:15]([O:17][C:18](=[O:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C@H:14]([CH3:26])[O:13][C:11]1=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 11221893Wrypvzdhvrcrog-xjksgupxsa-HCID 178418361HCID 178418361, compound

Product 1

HCID 11473679(2S,3R,5R)-2-methyl-6-oxotetrahydro-2H-pyran-3,5-diyl dibenzoateYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The compound (VIII) (6.1 g, 17.31 mmol) is dissolved in EtOAc (300 ml) and then 10%-Pd/C (400 mg) is added and is stirred for 3 hours at a room temperature after being substituted with hydrogen gas. The reactant is filtered by using celite 545. The solution is vacuum concentrated and then the compound (IX) (5.2 g, 85%) is isolated using flash column chromatography (toluene/EtOAc, 10:1, v/v).

Workup

  1. filtrationThe reactant is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ddb53d3a2a08427385a58fb0b707629f
Source dataset
uspto-grants-2009_08
Patent number
US07576225B2

Reaction notes

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