HCID 178418361, compound → HCID 178455044, compound

HRID 516894Notes

Reaction equation

HRID 516894 reaction equation
[Si:1]([O:8][C:9]1[CH:52]=[CH:51][C:12]([CH2:13][CH:14]([C:41]([O:43]CC2C=CC=CC=2)=[O:42])[C:15]([C@H:27]2[CH2:32][CH2:31][C@@H:30]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH2:29][CH2:28]2)([OH:26])[C:16]([O:18]CC2C=CC=CC=2)=[O:17])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H][H]>[Pd].[C]>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][CH:14]([C:41]([OH:43])=[O:42])[C:15]([C@H:27]2[CH2:28][CH2:29][C@@H:30]([O:33][Si:34]([C:37]([CH3:38])([CH3:39])[CH3:40])([CH3:36])[CH3:35])[CH2:31][CH2:32]2)([OH:26])[C:16]([OH:18])=[O:17])=[CH:51][CH:52]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178455043HCID 178455043, compound

Product 1

HCID 178455044HCID 178455044, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 178418390HCID 178418390, compoundCatalyst

Procedure

To a solution of dibenzyl 3-(4-((tert-butyldimethylsilyl)oxy)benzyl)-2-(cis-4-((tert-butyldimethylsilyl)oxy)-cyclohexyl)-2-hydroxysuccinate (120 mg, 0.16 mmol) was added 10% Pd-carbon (25 mg) under a nitrogen gas stream. The atmosphere in the reaction vessel was replaced five times with nitrogen gas, the reaction vessel was filled with hydrogen gas, and the system was stirred under a hydrogen gas stream for 24 hr. The mixture was filtered through Celite pad, and the catalyst was washed with ethanol (10 ml×2). The filtrate was concentrated under reduced pressure to give the title compound as an oil (90 mg, yield 99%).

Workup

  1. filtrationThe mixture was filtered through Celite pad
  2. washthe catalyst was washed with ethanol (10 ml×2)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8fc6a4e0908c45e796e2277da8fdf3f3
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

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