Sodium Methoxide → HCID 178486031, Verbindung

HRID 2057336

Reaktionsgleichung

Reaktionsgleichung von HRID 2057336
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 178486031HCID 178486031, VerbindungAusbeute 105 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a17f48715be64cf5a60ec8e2eec018cf
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335687B2

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