[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][NH:5][CH2:4]1.[CH3:8][N:9]([CH2:13][C:14]#[CH:15])[C:10](=[O:12])[CH3:11].[CH2:16]=O.[OH-].[Na+]>O.O1CCOCC1.C(O)(=O)C>[CH3:1][O:2][CH:3]1[CH2:7][CH2:6][N:5]([CH2:16][C:15]#[C:14][CH2:13][N:9]([CH3:8])[C:10](=[O:12])[CH3:11])[CH2:4]1A mixture of 365 mg of (racemic)-3-methoxypyrrolidine, 480 mg of N-methyl-N-propargyl acetamide, 180 mg of paraformaldehyde, 0.6 ml of acetic acid, 20 ml of dioxane and cuprous chloride catalyst was stirred at reflux under argon for 1 hour. The mixture was treated with 3 ml of 5N sodium hydroxide and 2 ml of water and extracted twice with dichloromethane. The extracts were combined, concentrated and purified by chromatography (alumina), giving 610 mg of the desired product.
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