Sodium Hydroxide → HCID 18538597, compound

HRID 1726144Notes

Reaction equation

HRID 1726144 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2Br)[OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]([OH:15])[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68972594HCID 68972594, compound

Product 1

HCID 18538597HCID 18538597, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the above alcohol (610 mg, 1.6 mmol) in MeOH (5 mL) in a Parr flask was added 10% Pd/C (100 mg) under N2. The mixture was hydrogenated at room temperature under 1.5 atm H2 for 1 h. 3N NaOH (5 mL) was added and the mixture was extracted with CHCl3 (20 mL×2). The solution was filtered through a short pad of Celite® to give the 4-(hydroxy-pyridin-4-yl-methyl)-piperidine-1-carboxylic acid tert-butyl ester (380 mg, 81%) as a colourless oil.

Workup

  1. extractionthe mixture was extracted with CHCl3 (20 mL×2)
  2. filtrationThe solution was filtered through a short pad of Celite®

Sources & evidence

ORD record
ord-79c7bf232f244f7ca15a80f0b29116a5
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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