HCID 178418361, compound → HCID 178468871, compound

HRID 1035711Notes

Reaction equation

HRID 1035711 reaction equation
[C:1]([O:5][C:6](/[CH:8]=[CH:9]/[C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6]([CH2:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178468870HCID 178468870, compound

Product 1

HCID 178468871HCID 178468871, compoundYield 125.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.150 g of ethyl trans-4-[4-((E)-2-tert-butoxycarbonylvinyl)cyclohexyl]benzoate (0.42 mmol, 1 eq.) is dissolved in 15 mL of ethanol in a Parr bottle. 0.044 g of 10% palladium-on-charcoal (0.04 mmol, 0.1 eq.) is added and the medium is subjected to 50 psi of hydrogen for 5 hours. The medium is filtered through Whatman paper, washed with ethanol and evaporated to give 0.19 g of ethyl trans-4-[4-(2-tert-butoxycarbonylethyl)cyclohexyl]benzoate.

Workup

  1. filtrationThe medium is filtered through Whatman paper
  2. washwashed with ethanol
  3. customevaporated

Sources & evidence

ORD record
ord-5a68b6a3711c44e289627b29934ca33e
Source dataset
uspto-grants-2013_10
Patent number
US08546391B2

Reaction notes

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