Sodium hydride → 1-(1-Phenyl-cyclohexyl)-pyrrolidin-2-one

HRID 2235201Notes

Reaction equation

HRID 2235201 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:6].[H-].[Na+]>C1COCC1>[C:14]1([C:8]2([N:7]3[CH2:2][CH2:3][CH2:4][C:5]3=[O:6])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 592994904-Chloro-N-(1-phenyl-cyclohexyl)-butyramide

Product 1

HCID 592994471-(1-Phenyl-cyclohexyl)-pyrrolidin-2-oneYield 124.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve 4-chloro-N-(1-phenyl-cyclohexyl)-butyramide (Preparation 29) (0.15 g, 0.53 mmol) in THF (20 mL) and add NaH (0.21 g, 5.29 mmol. 65% wt). Stir and heat the reaction mixture to 70° C. under nitrogen. Continue to heat the reaction at 70° C. for over night then cool it to room temperature. Add water (20 mL), and extract the aqueous layer with dichloromethane (3×50 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 10-40% of EtOAc/Hexane) to give 0.16 g (89%) of the title compound as a colorless oil: Mass spectrum (ion spray): m/z=243.9 (M+).

Workup

  1. temperatureto heat
  2. customthe reaction at 70° C. for over night
  3. temperaturethen cool it to room temperature
  4. extractionAdd water (20 mL), and extract the aqueous layer with dichloromethane (3×50 mL)
  5. dry with materialCombine the organic layers and dry with Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. custompurify by flash column chromatography (silica gel, 10-40% of EtOAc/Hexane)

Sources & evidence

ORD record
ord-b3a4576371f743d79db5eb428a4619af
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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