(+)-Glyceraldehyde → N-((2S)-2-(3,4-dichlorophenyl)-4-{4[(2S)-2,3-dihydroxy-1-(2-furyl)propyl]-1-piperazinyl}-butyl)-N-methylbenzamide

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Reaction Conditions

Reaction Steps

2.08 g N-[(2S)-2-(3,4-dichlorophenyl)-4-(piperazinyl)butyl]-N-methylbenzamide (preparation see above under 1C) was dissolved in 100 ml ethanol and heated to approx. 50° C. 740 mg 2-furanboronic acid and 550 mg of an 80%-strength solution of D-glyceraldehyde in water were added to this initial solution. The resulting solution was heated to boiling at reflux for 10 hours. Then excess solvent was evaporated in a vacuum. Purification of the residue by column chromatography on silica gel (mobile solvent: dichloromethane/EtOH/NH4OH 87/11/2) yielded 2.1 g of the title compound as a beige foam, optical rotation [α]D20=−6.1° (c=1 in methanol); 1H-NMR (CDCl3, RT): 3.65 (d, 1H); 4.23 (ddd, 1H); 3.72 (dd, 1H); 3.78 (dd, 1H); 6.27 (d, 1H); 6.37 (1H); 7.42 (1H).

Provenance & Evidence