Potassium Carbonate → HCID 19779542, compound

HRID 2082096Notes

Reaction equation

HRID 2082096 reaction equation
C([O:4][N:5]([CH:9]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)[CH2:10]1)[C:6](=[O:8])[CH3:7])(=O)C.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:20][O:19][C:15]1[CH:14]=[C:13]([CH:11]2[CH2:10][CH:9]([N:5]([OH:4])[C:6](=[O:8])[CH3:7])[CH2:12]2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 11430Potassium Carbonate2×HCID 19779538HCID 19779538, compound

Product 1

HCID 19779542HCID 19779542, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-acetoxy-N-[3-(3-methoxyphenyl)cyclobutyl]acetamide, (34.8 mmol from above), in methanol (150 mL) was added K2CO3 (9.22 g, 69.6 mmol) and the heterogeneous mixture was stirred for 30 min. An additional portion of K2CO3 (4.50 g) was then added and the reaction was stirred an additional 30 min. It was then filtered through Celite and concentrated. The resulting residue was chromatographed (silica gel; ether) to afford 4.92 g (60% over four steps) of N-[3-(3-methoxyphenyl)cyclobutyl]-N-hydroxyacetamide as an orange oil.

Workup

  1. stirringthe reaction was stirred an additional 30 min
  2. filtrationIt was then filtered through Celite
  3. concentrationconcentrated
  4. customThe resulting residue was chromatographed (silica gel; ether)

Sources & evidence

ORD record
ord-3c4d9a2b4ae342a39980802103d9cc39
Source dataset
uspto-grants-1993_02
Patent number
US05187192

Reaction notes

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