Tetrahydrofuran → HCID 57938916, compound

HRID 730367Notes

Reaction equation

HRID 730367 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C@@H:8]([C:10]1[N:11]([CH3:22])[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=2)[N:14]=1)[CH3:9])=[O:6].C1COCC1.CC(C)([O-])C.[K+].CCOC(C)=O>O>[I:21][C:18]1[CH:19]=[CH:20][C:15]([C:13]2[N:14]=[C:10]([C@H:8]([N:7]3[CH2:2][CH2:3][CH2:4][C:5]3=[O:6])[CH3:9])[N:11]([CH3:22])[CH:12]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 57594249HCID 57594249, compound

Product 1

HCID 57938916HCID 57938916, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a 20-dram vial was added (R)-4-chloro-N-(1-(4-(4-iodophenyl)-1-methyl-1H-imidazol-2-yl)ethyl)butanamide and THF (10 mL). The vial was cooled to 0° C. under a nitrogen atmosphere and potassium t-butoxide (214 mg, 1.91 mmol) was added. The reaction was stirred for 1.5 h. To the reaction mixture was added EtOAc (50 mL) and water (10 mL). The organic layer was separated, dried over Na2SO4, filtered, and concentrated. The residue was then dissolved in dichloromethane and purified by silica gel chromatography (5-50% CH3CN/CH2Cl2) to afford 593 mg (86%) of (R)-1-(1-(4-(4-iodophenyl)-1-methyl-1H-imidazol-2-yl)ethyl)pyrrolidin-2-one as a white solid (M+H (m/z)=396).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was then dissolved in dichloromethane
  6. custompurified by silica gel chromatography (5-50% CH3CN/CH2Cl2)

Sources & evidence

ORD record
ord-bc5fe5e35b3342d28cf78b08f384d7b4
Source dataset
uspto-grants-2009_09
Patent number
US07582668B2

Reaction notes

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