Cyclobutanone → HCID 11501983, compound

HRID 2386940Notes

Reaction equation

HRID 2386940 reaction equation
[CH3:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:14][CH:13]=2)[C:10](=[O:25])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:26]1(=O)[CH2:29][CH2:28][CH2:27]1>CO.[Cl-].[Zn+2].[Cl-].C([BH3-])#N.[Na+]>[CH:26]1([N:22]2[CH2:23][CH2:24][CH:19]([O:18][C:15]3[CH:14]=[CH:13][C:12]([N:11]4[C:10](=[O:25])[C:9]5[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=5)[N:3]=[C:2]4[CH3:1])=[CH:17][CH:16]=3)[CH2:20][CH2:21]2)[CH2:29][CH2:28][CH2:27]1

Participants

6

Reactant 2

HCID 14496CyclobutanoneHCID 23151166HCID 23151166, compound

Product 1

HCID 11501983HCID 11501983, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3007855ZincchlorideSolventHCID 5003444Sodium cyanoborohydrideSolvent

Procedure

2-methyl-3-[4-(4-piperidinyloxy-)phenyl}-4(3H)-quinazolinone (370 mg, 1.10 mmol) and cyclobutanone (155 mg, 2.20 mmol) were dissolved in a 0.5M methanol solution (6 mL) of zinc(II) chloride and sodium cyanoborohydride, and stirred at room temperature for 1 Hour. The solvent was distilled off under reduced pressure, ethyl acetate and distilled water were added, the mixture was extracted with ethyl acetate, and the organic phase washed with distilled water. After drying with anhydrous sodium sulfate, the product was purified by silica gel column chromatography (chloroform/methanol=30/1), and the title compound (165 mg, 39%) was obtained as a colorless solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, ethyl acetate
  2. distillationdistilled water
  3. additionwere added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washthe organic phase washed with distilled water
  6. dry with materialAfter drying with anhydrous sodium sulfate
  7. customthe product was purified by silica gel column chromatography (chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-a00ad9664b314ab7905b8a073bbad5d5
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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