Sodium Methoxide → HCID 178486031, compound

HRID 25661

Reaction equation

HRID 25661 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:22])[CH:9]1[CH2:14][CH2:13][C:12](=[CH:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]([CH3:22])[C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 225676825-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexylidene]-pentanoic acid

Product 1

HCID 178486031HCID 178486031, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5.0 g (16.1 mmol) 5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexylidene]-pentanoic acid in 50 ml methanol were hydrogenated with 0.5 g 10% Pd/C in the presence of 0.94 ml (16.9 mmol, 1.05 eq) sodium methanolate for 1 h at RT. After filtration and evaporation of the solvent, the residue was dissolved in ether and acidified by adding 1M HCl. The organic phase was extracted with water, dried over MgSO4 and evaporated to give 5.3 g (quant) trans-5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexyl]-pentanoic acid as light yellow oil, MS: (312 MH+).

Workup

  1. filtrationAfter filtration and evaporation of the solvent
  2. dissolutionthe residue was dissolved in ether
  3. additionby adding 1M HCl
  4. extractionThe organic phase was extracted with water
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-98cc4ac2c6584376b9b7374539a07143
Source dataset
uspto-grants-2005_02
Patent number
US06858651B2

Linked notes

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