Ammonium formate → 1211758-73-4

HRID 450565Notes

Reaction equation

HRID 450565 reaction equation
[N+:1]([C:4]1[C:5]([O:10][CH:11]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[C:5]([O:10][CH:11]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12]2)=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69669257HCID 69669257, compound

Product 1

HCID 696690941211758-73-4Yield 92%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Palladium hydroxide on carbon (20%, 0.071 g, 0.51 mmol) was added into a solution of tert-butyl 3-(3-nitropyridin-2-yloxy)azetidine-1-carboxylate (3.0 g, 10.2 mmol) and ammonium formate (3.20 g, 50.8 mmol) in ethanol (100 mL). The solution was stirred at ambient temperature for 18 hours, filtered through Celite and concentrated in vacuo. The crude product was extracted with chloroform (×3) and the combined organic fractions concentrated in vacuo to yield pale brown solid (2.48 g, 92%).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated in vacuo
  3. extractionThe crude product was extracted with chloroform (×3)
  4. concentrationthe combined organic fractions concentrated in vacuo

Sources & evidence

ORD record
ord-ae5286ab3f9544f78a077451c8e648ca
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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