HCID 14206207, compound → HCID 14482873, compound

HRID 329507Notes

Reaction equation

HRID 329507 reaction equation
C([O:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][O:11][C@H:10]1[CH2:15][O:16][C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C1C=CC=CC=1>C(O)C.[Pd].[H][H]>[OH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][O:11][C@H:10]1[CH2:15][O:16][C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 1

HCID 14206207HCID 14206207, compound

Product 1

HCID 14482873HCID 14482873, compoundYield 90.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

3.513 g of (2S, 3R)-3-benzyloxy-2-triphenylmethoxymethyltetrahydropyran (prepared as described in Preparation 23) were dissolved in 120 ml of ethanol and hydrogenated at room temperature for 30 hours in the presence of 1.852 g of 10% w/w palladium on activated carbon in a Paal's apparatus at a hydrogen pressure of 4 atmospheres (about 4 bars). The catalyst was filtered off and the filtrate was freed from the solvent by evaporation under reduced pressure. The residue was subjected to column chromatography through 90 g of silica gel, 2.557 g of the title compound were obtained, as a colorless oil, from those fractions eluted with a 7:1 by volume mixture of hexane and ethyl acetate.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was freed from the solvent by evaporation under reduced pressure

Sources & evidence

ORD record
ord-2b25c1fa0238448abbd7858d4e8b9c94
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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