HCID 178418361, compound → HCID 178455318, compound

HRID 516883Notes

Reaction equation

HRID 516883 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([OH:51])([CH:26]([C@H:37]2[CH2:42][CH2:41][C@@H:40]([O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[CH2:39][CH2:38]2)[C:27]([O:29]CC2C=CC=CC=2)=[O:28])[C:16]([O:18]CC2C=CC=CC=2)=[O:17])[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][C@@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]([OH:51])([CH:26]([C@H:37]2[CH2:38][CH2:39][C@@H:40]([O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:45])[CH3:46])[CH2:41][CH2:42]2)[C:27]([OH:29])=[O:28])[C:16]([OH:18])=[O:17])[CH2:13][CH2:14]1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178455317HCID 178455317, compound

Product 1

HCID 178455318HCID 178455318, compoundYield 129.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of dibenzyl 2,3-bis(cis-4-((tert-butyldimethylsilyl)oxy)cyclohexyl)-2-hydroxysuccinate (500 mg, 0.38 mmol) in ethanol (15 ml) was added 10% Pd-carbon (150 mg) under a nitrogen gas stream. The atmosphere in the reaction vessel was replaced five times with nitrogen gas and was filled with hydrogen gas, and the contents in the reaction vessel were stirred under a hydrogen gas stream for 24 hr. The catalyst was collected by filtration through Celite pad and was washed with ethanol (50 ml×2). The filtrate was concentrated under reduced pressure to give the title compound as a colorless solid (275 mg, yield 73%).

Workup

  1. filtrationThe catalyst was collected by filtration through Celite pad
  2. washwas washed with ethanol (50 ml×2)
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-585f60934252483191188d089e015c33
Source dataset
uspto-grants-2015_08
Patent number
US09115079B2

Reaction notes

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