Sodium hydride → 1-(1-Methylcyclohexyl)pyrrolidin-2-one

HRID 2235225Notes

Reaction equation

HRID 2235225 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1([CH3:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:6].[H-].[Na+]>C1COCC1>[CH3:14][C:8]1([N:7]2[CH2:2][CH2:3][CH2:4][C:5]2=[O:6])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 633083354-chloro-N-(1-methylcyclohexyl)butanamide

Product 1

HCID 592994351-(1-Methylcyclohexyl)pyrrolidin-2-oneYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Dissolve 4-chloro-N-(1-methylcyclohexyl)butanamide (1.35 g, 6.20 mmol) in anhydrous THF (100 mL) and add NaH (1.24 g, 31.00 mmol, 60% wt in oil). Heat and stir the reaction mixture at 60° C. overnight then cool it to room temperature. Add water (50 mL) carefully and extract the aqueous with EtOAc (3×200 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 20-70% of EtOAc-Hexane) to give 0.64 g (57%) of the title compound as a colorless oil. 1H NMR (CDCl3) δ 3.41 (t, 2H), 2.34 (t, 2H), 2.26 (m, 2H), 1.92 (m, 2H), 1.32-1.56 (m, 8H), 1.26 (s, 3H).

Workup

  1. temperatureHeat
  2. temperaturethen cool it to room temperature
  3. extractionAdd water (50 mL) carefully and extract the aqueous with EtOAc (3×200 mL)
  4. dry with materialCombine the organic layers and dry with Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. custompurify by flash column chromatography (silica gel, 20-70% of EtOAc-Hexane)

Sources & evidence

ORD record
ord-0c699a3c2cc74cacbbd77ae5c1a98b3e
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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