((2R)-1-methylpyrrolidin-2-yl)methanol → (1R/S,2R)-2-Hydroxymethyl-1-(isoxazol-3-ylcarbamoylmethyl)-1-methyl-pyrrolidinium bromide
Reaction equation
[Br:1][CH2:2][C:3]([NH:5][C:6]1[CH:10]=[CH:9][O:8][N:7]=1)=[O:4].[CH3:11][N:12]1[CH2:16][CH2:15][CH2:14][C@@H:13]1[CH2:17][OH:18]>C(#N)C>[Br-:1].[OH:18][CH2:17][C@H:13]1[CH2:14][CH2:15][CH2:16][N+:12]1([CH2:2][C:3](=[O:4])[NH:5][C:6]1[CH:10]=[CH:9][O:8][N:7]=1)[CH3:11]Participants
4
Procedure
To a solution of 2-bromo-N-isoxazol-3-yl-acetamide (Intermediate A) (3.9 g, 191 mmol) in acetonitrile (95 ml) is added ((R)-1-methyl-pyrrolidin-2-yl)-methanol (2.2 g, 191 mmol) in acetonitrile (5 ml). The reaction mixture is stirred at room temperature for 3 hours and then the solvent is removed in vacuo. The resulting oil is taken up in acetonitrile and ethyl acetate is then added. The resulting cloudy solution is stirred at room temperature for 30 minutes. There after, the supernatant is decanted off and the solid is dried under vacuum over two days to afford the titled compound.