1-(5-Nitropyridin-2-yl)azetidin-3-ol → 1-(5-Aminopyridin-2-yl)azetidin-3-ol

HRID 1948780Notes

Reaction equation

HRID 1948780 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][N:7]=2)[CH2:3]1.[H][H]>C(O)C.[Pd]>[NH2:12][C:9]1[CH:8]=[N:7][C:6]([N:4]2[CH2:3][CH:2]([OH:1])[CH2:5]2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 529372641-(5-Nitropyridin-2-yl)azetidin-3-olHCID 178418361HCID 178418361, compound

Product 1

HCID 574315251-(5-Aminopyridin-2-yl)azetidin-3-olYield 34.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 0.34 g (1.74 mmol) of 2-(3-hydroxyazetidin-1-yl)-5-nitropyridine, prepared in the preceding stage, and of 9 mg of Pd/C at 10% in 10 ml of ethanol is stirred vigorously at 20° C. under 5 atmospheres of hydrogen for 4 hours. After this period of time, the mixture is filtered through a celite buffer and then concentrated under reduced pressure. The resulting product is purified by silica column chromatography, elution being carried out with a mixture of dichloromethane and methanol. 0.1 g of the expected product is thus obtained, which product will be used as it is in the subsequent synthesis.

Workup

  1. customprepared in the preceding stage
  2. waitAfter this period of time
  3. filtrationthe mixture is filtered through a celite buffer and
  4. concentrationthen concentrated under reduced pressure
  5. customThe resulting product is purified by silica column chromatography, elution
  6. additionbeing carried out with a mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-fac3cd886ed54a1aa6f2d31b4617b238
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

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