Sodium Bicarbonate → N-[1-(4-methyl-2-pyridylmethyl)piperidin-4-yl]-2-cyclopentyl-2-hydroxy-2-phenylacetamide

HRID 366417

Reaktionsgleichung

Reaktionsgleichung von HRID 366417
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]=O)[CH:3]=1.[NH:10]1[CH2:15][CH2:14][CH:13]([NH:16][C:17](=[O:31])[C:18]([CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)([OH:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C.C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][N:10]2[CH2:11][CH2:12][CH:13]([NH:16][C:17](=[O:31])[C:18]([CH:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)([OH:25])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:14][CH2:15]2)[CH:3]=1

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 100118944-Methylpyridine-2-carbaldehydeHCID 10662143N-(piperidin-4-yl)-2-cyclopentyl-2-hydroxy-2-phenylacetamide

Produkt 1

HCID 23289913N-[1-(4-methyl-2-pyridylmethyl)piperidin-4-yl]-2-cyclopentyl-2-hydroxy-2-phenylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

75 Milligrams of 4-methyl-2-pyridinecarbaldehyde, 58.3 mg of N-(piperidin-4-yl)-2-cyclopentyl-2-hydroxy-2-phenylacetamide and 12 mg of acetic acid were dissolved in 10 ml of dichloroethane. To the solution 68 mg of sodium triacetoxyborohydride was added at room temperature, followed by an hour's stirring at the same temperature. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution, extracted with chloroform, dried over anhydrous magnesium sulfate and removed of the solvent by reduced pressure distillation. The residue was purified by preparative thin layer chromatography [Kieselgel™ 60F254Art 5744 (Merck), chloroform/methanol=9/1] to give 49.5 mg of the title compound as a white solid.

Aufarbeitung

  1. waitfollowed by an hour
  2. extractionextracted with chloroform
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customremoved of the solvent by reduced pressure distillation
  5. customThe residue was purified by preparative thin layer chromatography [Kieselgel™ 60F254Art 5744 (Merck), chloroform/methanol=9/1]

Quellen und Nachweise

ORD-Eintrag
ord-e6be6a68ac3f4643b4f05d94da177b6e
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130232

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