1-[(5-Hydroxy-2-pyridinyl)carbonyl]-piperidine → 6-Piperidin-1-ylmethyl-pyridin-3-ol

HRID 30459Notes

Reaction equation

HRID 30459 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=O)=[N:6][CH:7]=1>C1COCC1>[NH3:6].[N:10]1([CH2:8][C:5]2[N:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 445154541-[(5-Hydroxy-2-pyridinyl)carbonyl]-piperidine

Product 2

HCID 222AmmoniaYield 4%HCID 445154576-Piperidin-1-ylmethyl-pyridin-3-olYield 37.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (5-hydroxy-pyridin-2-yl)-piperidin-1-yl-methanone (1.30 g, 6.31 mmol) in THF (100 mL) was added borane-dimethylsulfide complex (1.75 mL, 18.9 mmol). After 18 h the solvent was removed and the residue was diluted with MeOH (50 mL) and heated to 60° C. After 2 h the solvent was evaporated and chromatography of the residue (SiO2: 4-8% 2 M NH3 in MeOH/DCM) gave the title compound as an oil (0.225 g, 17%).

Workup

  1. customAfter 18 h the solvent was removed
  2. additionthe residue was diluted with MeOH (50 mL)
  3. customAfter 2 h the solvent was evaporated

Sources & evidence

ORD record
ord-7ea993fe24364ba0b9d853afe0081f12
Source dataset
uspto-grants-2008_09
Patent number
US07423147B2

Reaction notes

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