Sodium hydride → HCID 11515332, compound

HRID 2235266Notes

Reaction equation

HRID 2235266 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][NH:7][C:6]1=[O:10].[H-].[Na+].Br[CH:19]1[CH2:24][CH2:23][CH2:22][CH:21]=[CH:20]1.C(=O)(O)[O-].[Na+]>C1COCC1>[CH:24]1([N:7]2[CH2:8][CH2:9][CH:5]([CH2:4][C:3]3[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:2]=3[Cl:1])[C:6]2=[O:10])[CH2:23][CH2:22][CH2:21][CH:20]=[CH:19]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 1370573-BromocyclohexeneHCID 516892Sodium BicarbonateHCID 59299392HCID 59299392, compound

Product 1

HCID 11515332HCID 11515332, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Charge a flask with 3-(2,4-dichloro-benzyl)-pyrrolidin-2-one (Preparation 19) (100 mg, 0.41 mmol), dissolve in THF (4 mL) and cool to 0° C. under nitrogen. Add NaH (15 mg, 0.61 mmol) and stir at 0° C. for 20 minutes. Add 3-bromo-cyclohexene (198 mg, 1.23 mmol) and stir at room temperature overnight. Pour into saturated aqueous sodium bicarbonate and extract with methylene chloride. Dry over sodium sulfate, filter and concentrate. Purify residue over silica gel (5:1 hexanes:ethyl acetate) to afford 68 mg (51%) of the title compound as a white solid. Mass spectrum (apci) m/z=324.1 (M+H).

Workup

  1. extractionextract with methylene chloride
  2. dry with materialDry over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-7ba7d77066c04bb2963bc484b57cef92
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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