HCID 131733339, compound → HCID 131733338, compound

HRID 516876Notes

Reaction equation

HRID 516876 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH:15]([C:26]([O-:28])=[O:27])[C:16]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)([OH:20])[C:17]([O-:19])=[O:18])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd].[C]>[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH:15]([C:26]([OH:28])=[O:27])[C:16]([CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)([OH:20])[C:17]([OH:19])=[O:18])[CH2:11][CH2:10]1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 131733339HCID 131733339, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131733338HCID 131733338, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of a diastereomeric mixture (330 mg, 0.55 mmol) of dibenzyl 3-(4-((tert-butyldimethylsilyl)oxy)cyclohexyl-2-cyclopentyl-2-hydroxysuccinate in ethanol (10 ml) was added 10% Pd carbon (150 mg) under a nitrogen gas stream. The atmosphere in a reaction vessel for the mixture was replaced five times with nitrogen gas, the reaction vessel was filled with hydrogen gas, and the contents of the reaction vessel were stirred for 24 hr under a hydrogen gas stream. The catalyst was collected by filtration through Celite pad and was washed with ethanol, and the filtrate was concentrated under reduced pressure to give the title compound as a colorless solid (190 mg, yield 83%).

Workup

  1. customThe atmosphere in a reaction vessel for the mixture was replaced
  2. filtrationThe catalyst was collected by filtration through Celite pad
  3. washwas washed with ethanol
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dc7e80b558524d0693fba2277e0f5e51
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

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