O-methylhydroxylammonium chloride → 1-(t-Butoxycarbonyl)-3-methoxyiminopyrrolidine
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][O:15][NH3+:16].[Cl-]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10](=[N:16][O:15][CH3:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
27 ml of anhydrous pyridine were added to a mixture of 2.0 g of 1-(t-butoxycarbonyl)-3-pyrrolidone and 992 mg of o-methylhydroxylamine hydrochloride, and the mixture was kept stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off and saturated aqueous sodium bicarbonate solution was added to the residue until it was basic. The mixture was extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate and concentrated. The residue was chromatographed over silica gel, using a 3/1 mixture of benzene and ethyl acetate as eluent, giving 2.3 g of 1-(t-butoxycarbonyl)-3-methoxyiminopyrrolidine as a mixture of syn- and anti-isomers.