Trifluoroacetic acid → Azetidin-3-yl(3,5-difluorophenyl)methanone

HRID 602665Notes

Reaction equation

HRID 602665 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:21])[CH:20]=1)[C:5]([CH:7]1[CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]1)=[O:6].C(O)(C(F)(F)F)=O>Cl.O1CCOCC1>[NH:9]1[CH2:10][CH:7]([C:5]([C:4]2[CH:18]=[C:19]([F:21])[CH:20]=[C:2]([F:1])[CH:3]=2)=[O:6])[CH2:8]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670659051,1-Dimethylethyl 3-(3,5-difluorobenzoyl)-1-azetidinecarboxylate

Product 1

HCID 67065914Azetidin-3-yl(3,5-difluorophenyl)methanone

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 400 mg (1.35 mmol) of tert-butyl 3-(3,5-difluorobenzoyl)azetidine-1-carboxylate in 6 mL of HCl in dioxane (4M) and 2.5 mL of TFA was stirred for 4 h at 50° C. The reaction mixture was concentrated, and the residue was washed with hexanes/ether (1/1) to afford the title compound. Mass Spectrum: m/e=199 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe residue was washed with hexanes/ether (1/1)

Sources & evidence

ORD record
ord-690a8d1c6f9d4259be1f5ae100ea3c17
Source dataset
uspto-grants-2011_03
Patent number
US07906503B2

Reaction notes

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