Water → 1-Benzyl-3-methylpyrrolidin-3-OL

HRID 2424835Notes

Reaction equation

HRID 2424835 reaction equation
C[Mg]Br.[CH2:4]([N:11]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O.[CH2:18](OCC)C>O1CCCC1>[CH2:4]([N:11]1[CH2:15][CH2:14][C:13]([CH3:18])([OH:16])[CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 698901-Benzyl-3-pyrrolidinoneHCID 178418573HCID 178418573, compound

Product 1

HCID 186296481-Benzyl-3-methylpyrrolidin-3-OL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (4 ml of 3M solution in diethyl ether) was added dropwise to a solution of 1-benzylpyrrolidin-3-one (1.75 g) in tetrahydrofuran (50 ml) at 0° C. The mixture was stirred at 0° C. for 1 hour before water and diethyl ether were added and the layers separated. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash column chromatography (SiO2, 5% methanol/dichloromethane as eluent) to afford the subtitle compound as a pale brown oil (0.8 g).

Workup

  1. additionwere added
  2. customthe layers separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash column chromatography (SiO2, 5% methanol/dichloromethane as eluent)

Sources & evidence

ORD record
ord-62e819b1943840e0ab45c4d064415ad0
Source dataset
uspto-grants-2011_06
Patent number
US07964616B2

Reaction notes

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