Sodium borohydride → Methyl (3r,4r)-1-[2-(thien-2-ylthio)ethyl]-4-[3-(r,s)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

0.125 g of sodium borohydride and 0.066 g of molybdenum oxide are added with stirring and under an inert atmosphere, at a temperature in the region of −5° C., to a solution of 0.17 g of methyl (3R,4R)-1-[2-(thien-2-ylthio)ethyl]-4-[3-hydroxyimino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate in 10 cm3 of methanol. After 5 hours at a temperature in the region of 20° C., 0.125 g of sodium borohydride and 0.066 g of molybdenum oxide are again added and then the reaction mixture is stirred for an additional 18 hours at a temperature in the region of 20° C. The resulting mixture is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained is purified by chromatography under a pressure of 50 kPa of nitrogen on a column of silica gel (particle size 20-45 μ; mass 34 g; diameter of the column 2.3 cm), elution being carried out with a dichloromethane/methanol (95/5 by volume) mixture. Fractions 220 to 365 (containing the purified product) are combined and then concentrated to dryness under the above conditions to afford 0.06 g of methyl (3R,4R)-1-[2-(thien-2-ylthio)ethyl]-4-[3-(R,S)-amino-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate.

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