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

HRID 1905921Notes

Reaction equation

HRID 1905921 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.[CH3:14][Mg]I>>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([OH:13])([CH3:14])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 698901-Benzyl-3-pyrrolidinoneHCID 178418373HCID 178418373, compound

Product 1

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

Procedure

1-Benzyl-3-pyrrolidone [J. Org. Chem., 30., 740 (1965)] was allowed to react with methylmagnesium iodide to give 1-benzyl-3-hydroxy-3-methylpyrrolidine as an oil, b.p. 106° C./0.5 mmHg. This compound was treated with a mixture of acetonitrile and concentrated sulfuric acid under ice cooling to give 3-acetylamino-1-benzyl-3-methylpyrrolidine, m.p. 105°-106° C. This compound was hydrogenated catalytically in the presence of 5% palladium-carbon to give 3-acetylamino-3-methylpyrrolidine as an oil.

Sources & evidence

ORD record
ord-c2d74861b553463e9856bc3c698246a8
Source dataset
uspto-grants-1987_03
Patent number
US04649144

Reaction notes

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