Sodium Hydroxide → 1-Benzyl-4-methylpyrrolidin-3-amine

Reaction equation

[OH-].[Na+].[CH2:3]([N:10]1[CH2:14][CH:13]([CH3:15])[C:12](=[N:16]O)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C.[Ni]>[CH2:3]([N:10]1[CH2:14][CH:13]([CH3:15])[CH:12]([NH2:16])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Procedure

90 ml of a 20% w/v aqueous solution of sodium hydroxide were added to a solution of 12 g (0.059 mole) of 1-benzyl-3-(hydroxyimino)-4-methylpyrrolidine [prepared as described in Step (5) above] dissolved in 100 ml of ethanol. 23.9 g of Raney nickel (about 50%) were gradually added to the mixture, whilst vigorously stirring it. After the reaction mixture had been stirred for 3 hours, it was filtered. The upper layer of the filtrate was separated and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel eluted with methanol, to give 80 g of 1-benzyl-3-amino-4-methylpyrrolidine as a pale yellow liquid.