Water → Methyl 1-(4-nitrophenyl)azetidine-3-carboxylate

HRID 624249Notes

Reaction equation

HRID 624249 reaction equation
Cl.[NH:2]1[CH2:5][CH:4]([C:6]([O:8][CH3:9])=[O:7])[CH2:3]1.CN1CCOCC1.F[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.O>CN(C)C=O>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([N:2]2[CH2:5][CH:4]([C:6]([O:8][CH3:9])=[O:7])[CH2:3]2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 9590p-FluoronitrobenzeneHCID 21100040Methyl azetidine-3-carboxylate hydrochloride

Product 1

HCID 53402913Methyl 1-(4-nitrophenyl)azetidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl azetidine-3-carboxylate hydrochloride (1.236 g, 8.15 mmol) and N-methylmorpholine (2.338 ml, 21.26 mmol) in dimethylformamide (10 mL) was treated with a solution of 1-fluoro-4-nitrobenzene (1 g, 7.09 mmol) in dimethylformamide (7 mL) and the reaction was allowed to stir at room temperature for 60 hours. Water (50 mL) was added and the resulting suspension was stirred 10 minutes and filtered. The collected solid was washed with water and dried under vacuum. Flash chromatography of the collected solid provided the title compound.

Workup

  1. stirringthe resulting suspension was stirred 10 minutes
  2. filtrationfiltered
  3. washThe collected solid was washed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-d2f1be45ac304df7b928eb63253d808b
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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