Acetic Acid → 1-[(3,4-Dimethoxyphenyl)methyl]-4-(hydroxymethyl)pyrrolidin-2-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:6][N:7]1[CH2:11][CH:10]([C:12](OCC)=[O:13])[CH2:9][C:8]1=[O:17].[BH4-].[Na+].[BH4-].C(O)(=O)C>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[CH2:6][N:7]1[CH2:11][CH:10]([CH2:12][OH:13])[CH2:9][C:8]1=[O:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
8.0 g of 1-(3,4-dimethoxybenzyl)-4-ethoxycarbonyl-pyrrolidin-2-one were dissolved in 100 ml of methanol. Over a period of 20 minutes, at 0°-10° C., a solution of 2.8 g of sodium borohydride in 30 ml of water was added dropwise, while mechanically stirring, and the mixture was stirred for 5 hours more at 0°-10° C. The excess borohydride was then carefully decomposed by the addition of glacial acetic acid up to a pH of 5 and until the development of gas had ceased, and the methanol was distilled off in vacuo. Some water was added, and the reaction product was taken up in methylene chloride. The methylene chloride phase was then washed with water, dried and evaporated. The residue was chromatographed on silica gel (eluant: methylene chloride/methanol 98:2). Finally, 4.8 g (62% of theory) of the title compound were obtained from the eluate.
Workup
- stirringthe mixture was stirred for 5 hours more at 0°-10° C
- distillationthe methanol was distilled off in vacuo
- additionSome water was added
- washThe methylene chloride phase was then washed with water
- customdried
- customevaporated
- customThe residue was chromatographed on silica gel (eluant: methylene chloride/methanol 98:2)
Sources & evidence
- ORD record
- ord-a9d8524d261a4800a0950f92f3ddbf09
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04581364
Reaction notes
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