Tetrahydrofuran → HCID 18962891, compound

HRID 1707228Notes

Reaction equation

HRID 1707228 reaction equation
O1CCCC1.[CH3:6][C:7]([N:16]1[CH2:20][C:19]([CH2:22]Br)([CH3:21])[CH:18]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])[C:17]1=[O:31])([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)[CH3:8].C[O-].[Na+]>CO>[CH3:6][C:7]([N:16]1[CH2:20][C:19]2([CH3:22])[C:18]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])([CH2:21]2)[C:17]1=[O:31])([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)[CH3:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 18962885HCID 18962885, compound

Product 1

HCID 18962891HCID 18962891, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 20 ml of tetrahydrofuran were added 0.7 g of 1-[1-methyl-1-(3-chlorophenyl)ethyl]-4-bromomethyl-4-methyl-3-(2-fluorophenyl)pyrrolidine-2-one and 0.35 g of a 28% methanol solution of sodium methoxide, and the solution was then stirred at room temperature for 1 hour. After the solvent was distilled off, ice water was added to the solution, and extraction was then made with ethyl acetate. Next, the resultant extract was dried over anhydrous sodium sulfate, and after concentration, column chromatography was done to obtain 0.5 g of the desired 3-[1-methyl-1-(3-chlorophenyl)ethyl]-5-methyl-1-(2-fluorophenyl)-3-azabicyclo[3.1.0]hexane-2-one.

Workup

  1. distillationAfter the solvent was distilled off
  2. additionice water was added to the solution, and extraction
  3. extractionNext, the resultant extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationafter concentration, column chromatography

Sources & evidence

ORD record
ord-bbb9d39e511b426daffd167319c568a7
Source dataset
uspto-grants-1994_10
Patent number
US05352655

Reaction notes

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