Sodium Hydroxide → HCID 23289921, compound

HRID 366419Notes

Reaction equation

HRID 366419 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:34])[C:21]([CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)([OH:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:15][CH2:14]2)[CH:7]=1)=O)C.[H-].[Li+].[Al+3].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[OH:3][CH2:4][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH2:12][N:13]2[CH2:14][CH2:15][CH:16]([NH:19][C:20](=[O:34])[C:21]([CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)([OH:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:18]2)[CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 23289923HCID 23289923, compound

Product 1

HCID 23289921HCID 23289921, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 92 mg of N-[1-(4-ethoxycarbonyl-2-pyridylmethyl)piperidin-4-yl]-2-cyclopentyl-2-hydroxy-2-phenylacetamide in 2 ml of tetrahydrofuran, 15 mg of aluminium lithium hydride was added at 0° C., followed by 2 hours' stirring at room temperature. To the reaction mixture 30 μl of 3N sodium hydroxide solution and anhydrous sodium sulfate were added, and the mixture was filtered with celite. Distilling the solvent off under reduced pressure, the residue was purified by preparative thin layer chromatography [Kieselgel™ 60F254, Art 5744 (Merck), chloroform/methanol=10/1] to give 36 mg of the title compound as a colorless oily substance.

Workup

  1. filtrationthe mixture was filtered with celite
  2. distillationDistilling the solvent off under reduced pressure
  3. customthe residue was purified by preparative thin layer chromatography [Kieselgel™ 60F254, Art 5744 (Merck), chloroform/methanol=10/1]

Sources & evidence

ORD record
ord-076fcce737174cda8f6fe57c1a95d0e3
Source dataset
uspto-grants-2000_10
Patent number
US06130232

Reaction notes

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