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With oxygen; potassium hydroxide; In dimethyl sulfoxide; at 120℃; under 760.051 Torr; for 12h;Green chemistry;
General procedure: A mixture of benzamidine hydrochloride 1a (0.25mmol), cinnamaldehyde 2a (0.30mol) and KOH (0.50mmol, 2equiv.) was stirred in DMSO (1.0mL) under 1atm O2 atmosphere at 120C for 12h. After completion of the reaction (monitored by TLC), water (10mL) was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The combined organic layers were then dried over MgSO4, filtered, and then concentrated in vacuo. The residue was purified by flash chromatography on silica gel to give the desired product 3aa as a white solid (using the mixture of petroleum ether and ethyl acetate as eluents
(3R,4R,5S)-4-acetamido-5-(((E)-3-(4-fluorophenyl)allyl)amino)-3-((pentan-3-yl)oxy)cyclohexene-1-ene-1-carboxylic acid ethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
68%
With sodium cyanoborohydride; In methanol; ethanol; at 20℃; for 6h;
General procedure: The solution of <strong>[204255-11-8]oseltamivir phosphate</strong> (0.82 g, 2.0 mmol) and akind of aldehyde (2.4 mmol, 1.2 equiv) in 30 mL methanol andethanol (V : V 2 : 1) was stirred at room temperature for half anhour. And then, NaBH3CN (0.31 g, 5.0 mmol, 2.5 equiv) was addedslowly to the solution. After that, the mixture was stirred for 6 h atroom temperature. The solvent was removed under reduced pressure,water (30 mL) was added to the residue and extracted withethyl acetate (3 30 mL). The combined organic phasewas washedwith saturated sodium chloride (2 30 mL) and dried with anhydrousMgSO4 and concentrated under reduced pressure. Theconcentrated crude was purified by flash column chromatographyto obtain the corresponding pure intermediates 1a-1g.
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