N-methyl-2-pyrrolidone → HCID 66661710, compound

HRID 557860Notes

Reaction equation

HRID 557860 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:15][N:16]1CCCC1=O>CCOC(C)=O.[C-]#N.[Zn+2].[C-]#N.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[Zn]>[C:15]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1)#[N:16]

Participants

7

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 20110257Methyl 1-(4-chlorophenyl)cyclopropane-1-carboxylate

Product 1

HCID 66661710HCID 66661710, compoundYield 76%

Reagents, catalysts & solvents 4

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 178418851HCID 178418851, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A degassed mixture of methyl 1-(4-chlorophenyl)cyclopropanecarboxylate (4.748 g, 0.02254 mol), zinc cyanide (2.701 g, 0.02254 mol), bis(tri-t-butylphosphine)palladium (705 mg, 0.00135 mol) and zinc (265 mg, 0.00406 mol) powder in anhydrous N-methylpyrrolidinone (50.0 mL, 0.518 mol) was heated at 150° C. for 18 hours. The completion of the reaction is determined by LCMS and TLC. The reaction mixture was cooled to rt, diluted with EtOAc, filtered through a pad of celite and the solid was washed with EtOAc. The filtrate was washed with 2 N NH4OH (100 mL) and brine successively, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by Combiflash with 2-15% EtOAc/hexanes to give the product as a colorless oil (3.434 g, 76% in yield). LC/MS: (M+H)=202.1.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered through a pad of celite
  3. washthe solid was washed with EtOAc
  4. washThe filtrate was washed with 2 N NH4OH (100 mL) and brine successively
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by Combiflash with 2-15% EtOAc/hexanes

Sources & evidence

ORD record
ord-3804f04edc964846b250acd5dc370bf8
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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