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

HRID 1690064Notes

Reaction equation

HRID 1690064 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-ol

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 9 mg of Pd/C at 10% in 10 mL of ethanol is stirred vigorously at 20° C. under 5 atm of hydrogen for 4 hours. After this time, the mixture is filtered on a Celite pad and then concentrated at reduced pressure. The resultant product is purified by chromatography on a silica column, eluting with a mixture of dichloromethane and methanol. We thus obtain 0.1 g of the expected product, which will be used as it is in the rest of the synthesis.

Workup

  1. filtrationAfter this time, the mixture is filtered on a Celite pad
  2. concentrationconcentrated at reduced pressure
  3. customThe resultant product is purified by chromatography on a silica column
  4. washeluting with a mixture of dichloromethane and methanol
  5. customis in the rest of the synthesis

Sources & evidence

ORD record
ord-adefdc839dbc4fab97ac777b1538fb7c
Source dataset
uspto-grants-2012_04
Patent number
US08153650B2

Reaction notes

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