1-Benzyl-3-pyrrolidinone → 1-Benzyl-3-methylpyrrolidin-3-OL

HRID 1366520Notes

Reaction equation

HRID 1366520 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][Mg+].[Br-]>C1COCC1.CCOCC>[CH3:14][C:10]1([OH:13])[CH2:11][CH2:12][N:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 698901-Benzyl-3-pyrrolidinoneHCID 178418689HCID 178418689, compound

Product 1

HCID 186296481-Benzyl-3-methylpyrrolidin-3-OLYield 46%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of commercially available 1-(phenylmethyl)-3-pyrrolidinone (1.0 g, 5.71 mmol) in THF (30 mL) and ether (30 mL) at 0° C. was added MeMgBr (1.4 M solution in toluene:THF (3:1)) (6.1 mL, 8.65 mmol). The reaction was stirred at 0° C. for 1.5 hours, then quenched with water and extracted. Removed organic solvent in vacuo and extracted again with ether, dried organics (Na2SO4) and removed solvent in vacuo. Purified by RP-HPLC to provide racemic 3-methyl-1-(phenylmethyl)-3-pyrrolidinol as a yellow oil (0.501 g, 46%). LCMS: (M+H)+=192.3.

Workup

  1. customquenched with water
  2. extractionextracted
  3. extractionRemoved organic solvent in vacuo and extracted again with ether, dried organics (Na2SO4)
  4. customremoved solvent in vacuo
  5. customPurified by RP-HPLC

Sources & evidence

ORD record
ord-02dadb572e3743baa8b10a23872a71f6
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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