Dimethylformamide → tert-Butyl 3-(4-fluorophenoxy)azetidine-1-carboxylate

HRID 1477588Notes

Reaction equation

HRID 1477588 reaction equation
CN(C)C=O.S([O:16][CH:17]1[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]1)(C1C=CC(C)=CC=1)(=O)=O.[F:28][C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(OCC)(=O)C.O>[F:28][C:29]1[CH:34]=[CH:33][C:32]([O:16][CH:17]2[CH2:18][N:19]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:20]2)=[CH:31][CH:30]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 57351432tert-Butyl 3-(tosyloxy)azetidine-1-carboxylate

Product 1

HCID 101909068tert-Butyl 3-(4-fluorophenoxy)azetidine-1-carboxylateYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

An N,N-dimethylformamide solution (1.5 mL) of tert-butyl 3-(tosyloxy)azetidine-1-carboxylate (164 mg, 0.50 mmol), 4-fluorophenol (67.3 mg, 0.60 mmol), and cesium carbonate (116 mg, 0.60 mmol) was stirred at 80° C. for 16 hours. After completion of the reaction, water was added to the reaction solution and extraction with ethyl acetate from the resultant mixture was performed three times. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (97.4 mg, yield 73%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d413849aaeb94910b46c2aea2b4da8fb
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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