Ammonium Chloride → Tert-butyl 3-(3-fluorobenzoyl)azetidine-1-carboxylate

HRID 72404Notes

Reaction equation

HRID 72404 reaction equation
CON(C)[C:4]([CH:6]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:5].[F:18][C:19]1[CH:20]=[C:21]([Mg]Br)[CH:22]=[CH:23][CH:24]=1.[NH4+].[Cl-]>O1CCCC1>[F:18][C:19]1[CH:24]=[C:23]([CH:22]=[CH:21][CH:20]=1)[C:4]([CH:6]1[CH2:7][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH2:9]1)=[O:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21306970tert-Butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylateHCID 178505773HCID 178505773, compound

Product 1

HCID 69062376Tert-butyl 3-(3-fluorobenzoyl)azetidine-1-carboxylateYield 98.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution of tert-butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate (D26) (61.8 mg, 0.25 mmol) in dry tetrahydrofuran (2 ml), 3-Fluorophenylmagnesiumbromide (1M in tetrahyfrofuran) (0.506 ml, 0.506 mmol) was added dropwise the under stirring under N2 atmosphere. The reaction mixture was stirred at room temperature for 1 h then NH4Cl sat. sol. (10 ml) was added and the mixture was extracted with ethylacetate (3×20 ml). The organic layers were collected, dried with Na2SO4 and filtrated. The solvent was evaporated in vacuo to afford the title compound (D27) (69 mg).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. extractionthe mixture was extracted with ethylacetate (3×20 ml)
  3. customThe organic layers were collected
  4. dry with materialdried with Na2SO4
  5. filtrationfiltrated
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-41e54f92b7b4436dae0b089503594c72
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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