Potassium Carbonate → 3-(2-Formyl-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

HRID 1479007Notes

Reaction equation

HRID 1479007 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:10]([O:14][C:15]([N:17]1[CH2:20][CH:19]([OH:21])[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(Cl)Cl>[C:10]([O:14][C:15]([N:17]1[CH2:20][CH:19]([O:21][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylate2×

Product 1

HCID 896503653-(2-Formyl-phenoxy)-azetidine-1-carboxylic acid tert-butyl esterYield 46.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-fluoro-benzaldehyde (0.85 mL; 8.06 mmol; 1 eq.), 3-hydroxy-azetidine-1-carboxylic acid tert-butyl ester (1.54 g mg; 8.86 mmol; 1.1 eq.) and K2CO3 (2.23 g; 16.11 mmol; 2 eq.) in DMF (20 mL) was stirred at 120° C. for 16 hours. 3-Hydroxy-azetidine-1-carboxylic acid tert-butyl ester (279 mg; 1.61 mmol; 0.2 eq.) was added and the reaction mixture was stirred at room temperature for 2 days. The reaction mixture was diluted with DCM, washed with water then brine, dried over magnesium sulfate and concentrated in vacuo. Recrystallization from Et2O afforded the title compound (1.03 g, 46%) as a yellow solid. HPLC (max plot) 99.4%; Rt 4.07 min.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 2 days
  2. washwashed with water
  3. dry with materialbrine, dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customRecrystallization from Et2O

Sources & evidence

ORD record
ord-16f64e9084cf4f88a07226f84ec82bc9
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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