Ethanol → 1-(6-Aminopyridin-3-yl)azetidin-3-ol

HRID 1918854Notes

Reaction equation

HRID 1918854 reaction equation
[N+:1]([C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:13][CH:12]([OH:14])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.C(O)C>[Pd].CO>[NH2:1][C:4]1[N:9]=[CH:8][C:7]([N:10]2[CH2:11][CH:12]([OH:14])[CH2:13]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 592909581-(6-Nitro-pyridin-3-yl)-azetidin-3-ol

Product 1

HCID 580438121-(6-Aminopyridin-3-yl)azetidin-3-olYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 500-mL Parr hydrogenation bottle was charged with 128a (1.9 g, 9.6 mmol), 10% palladium on carbon (50% wet, 570 mg dry weight) and ethanol (100 mL). The bottle was evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken for 24 h on a Parr hydrogenation apparatus. The catalyst was removed by filtration through a pad of Celite 521 washing with 1:1 CH2Cl2:MeOH (500 mL). The resulting residue was purified by column chromatography eluting with a gradient of 100% DCM-100% 3:1 DCM:MeOH to afford a 70% yield (1.1 g) of 128b.

Workup

  1. customThe bottle was evacuated
  2. additioncharged with hydrogen gas to a pressure of 50 psi
  3. customThe catalyst was removed by filtration through a pad of Celite 521 washing with 1:1 CH2Cl2
  4. customThe resulting residue was purified by column chromatography
  5. washeluting with a gradient of 100% DCM-100% 3:1 DCM

Sources & evidence

ORD record
ord-87511df531f64d6e897ff68951eb9868
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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