Diethyl Ether → 1-Benzyl-3-methylpyrrolidin-3-OL

HRID 72115

Reaction equation

HRID 72115 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Mg+].[Br-].[CH3:17]COCC.[NH4+].[Cl-]>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH3:17])([OH:13])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 698901-Benzyl-3-pyrrolidinoneHCID 178418689HCID 178418689, compound

Product 1

HCID 186296481-Benzyl-3-methylpyrrolidin-3-OLYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 1-benzyl-3-pyrrolidinone (8.36 g, 47.7 mmol) in dry THF (100 mL) was cooled to −70° C. and 3 M MeMgBr in ether (30 mL, 90 mmol) was added over 5 min. The cooling bath was allowed to expire and the mixture was stirred overnight at rt. The mixture was poured into satd aq NH4Cl (300 mL) and extracted with ether (3×100 mL). The combined organic extracts were washed with brine (50 mL), dried over Na2SO4 and concentrated to leave 1-benzyl-3-methylpyrrolidin-3-ol (8.98 g) as an oil.

Workup

  1. extractionextracted with ether (3×100 mL)
  2. washThe combined organic extracts were washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1f033f80af3540c0ae85626730306c67
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Linked notes

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