Potassium Carbonate → HCID 89650147, compound

HRID 1479011Notes

Reaction equation

HRID 1479011 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]([CH2:21][OH:22])[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C([O-])(O)=O.[Na+]>[C:10]([O:14][C:15]([N:17]1[CH2:20][CH:19]([CH2:21][O:22][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])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Product 1

HCID 89650147HCID 89650147, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-fluoro-benzaldehyde (0.85 mL; 8.06 mmol; 1 eq.), 3-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester (1.66 g; 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 7 days. The reaction mixture was diluted with sat. aq. NaHCO3 and extracted with DCM (2×). The combined organic layer was washed with brine (2×), dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (heptane/EA, 95/5 to 60/40) afforded the title compound (810 mg, 35%) as a white solid. HPLC (max plot) 96.2%; Rt 4.15 min.

Workup

  1. extractionextracted with DCM (2×)
  2. washThe combined organic layer was washed with brine (2×)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by column chromatography (heptane/EA, 95/5 to 60/40)

Sources & evidence

ORD record
ord-73f318a128a144a2922acb04740cfc6e
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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