Ammonium formate → 3-(3-Fluorophenoxy)azetidine

HRID 1066903Notes

Reaction equation

HRID 1066903 reaction equation
C([N:14]1[CH2:17][CH:16]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C1COCC1.CO.[Pd]>[F:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[O:18][CH:16]1[CH2:17][NH:14][CH2:15]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 197996211-Benzhydryl-3-(3-fluorophenoxy)azetidine

Product 1

HCID 155219743-(3-Fluorophenoxy)azetidineYield 67%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.50 g of 1-benzhydryl-3-(3-fluoro-phenoxy)-azetidine in 10 mL of THF was added to a suspension of 10% Pd/C in methanol. Ammonium formate (4.6 g) were added portion wise and the reaction was heated under reflux for 3 h. The mixture was cooled, filtered through celite, and the filtrate was concentrated. The residue was triturated with CH2Cl2 and filtered. The filtrate was concentrated to give 0.840 g of the desired product.

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 3 h
  3. temperatureThe mixture was cooled
  4. filtrationfiltered through celite
  5. concentrationthe filtrate was concentrated
  6. customThe residue was triturated with CH2Cl2
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5711593f1aa94b75ac8b8f3ffe2c0d2e
Source dataset
uspto-grants-2001_06
Patent number
US06245799B1

Reaction notes

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