Sodium Hydroxide → Tert-butyl 4-(hydroxy(pyridin-3-yl)methyl)piperidine-1-carboxylate

HRID 1726142Notes

Reaction equation

HRID 1726142 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:16]2[C:17](Br)=[N:18][CH:19]=[CH:20][CH:21]=2)[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:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 722066791-Boc-4-[(2-Bromopyridin-3-yl)hydroxymethyl]piperidine

Product 1

HCID 18538796Tert-butyl 4-(hydroxy(pyridin-3-yl)methyl)piperidine-1-carboxylateYield 72.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of the above alcohol (470 mg, 1.27 mmol) in MeOH (4 ml) in a Parr flask was added 10% Pd/C (80 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 combined organic solution was filtered through a short pad of Celite® to give 4-(hydroxy-pyridin-3-yl-methyl)-piperidine-1-carboxylic acid tert-butyl ester (270 mg, 72%) as a colourless oil.

Workup

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

Sources & evidence

ORD record
ord-02022034896247d193c7fb97f4d02ecb
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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