2-[6-(Azidomethyl)-2-pyridyl]propan-2-ol → 2-(6-(Aminomethyl)pyridin-2-yl)propan-2-ol

HRID 876975Notes

Reaction equation

HRID 876975 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([OH:14])([CH3:13])[CH3:12])[N:6]=1)=[N+]=[N-]>CO.[Pd]>[OH:14][C:11]([C:7]1[N:6]=[C:5]([CH2:4][NH2:1])[CH:10]=[CH:9][CH:8]=1)([CH3:13])[CH3:12]

Participants

4

Reactant 1

HCID 866553202-[6-(Azidomethyl)-2-pyridyl]propan-2-ol

Product 1

HCID 667184282-(6-(Aminomethyl)pyridin-2-yl)propan-2-olYield 90.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Azidomethyl-6-(1-hydroxy-1-methylethyl)pyridine (5.88 g, 30.6 mmol) was dissolved in methanol (100 mL) and palladium (5% w/w on carbon) added. The suspension was gently agitated under a hydrogen atmosphere overnight, filtered though celite and concentrated to dryness to give 4.61 g (90%) of the amine as a colorless oil; NMR δH (400 MHz, CDCl3) 7.63 (1H, t, J 7.8 Hz), 7.19 (1H, d, J 7.8 Hz), 7.12 (1H, d, J 7.6 Hz), 3.93 (2H, s), 1.49 (6H, s); LC-MS Retention time 0.42 min, (M+H)+ 167.

Workup

  1. filtrationfiltered though celite and
  2. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5c7eb5756bfc451db5134e76a4843e18
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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