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Undesired 1,4-reduction could be avoided by lowering the reaction temperature
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Undesired 1,4-reduction could be avoided by lowering the reaction temperature.
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note
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To a solution of 40 mg (0.105 mmol) of (-)-17β-hydroxy-11-methoxytabersonine 20 in 2.4 ml of 10% methanol/ dichloromethane and 1.8 ml of a saturated aqueous solution of sodium bicarbonate at 0 °C was added 36 mg (0.209 mmol) of m-chloroperoxybenzoic acid. After stirring for 5 min at 0 °C, 0.30 ml (3.56 mmol) of 37% aqueous formaldehyde and 26 mg (0.418 mmol) of sodium cyanoborohydride were added and pH of the solution was adjusted to 3.0 with 10% hydrochloric acid in methanol. After stirring for 5 min, an additional 26 mg (0.418 mmol) of sodium cyanoborohydride was added and stirring was continued at room temperature for 30 min. Sodium carbonate was added to adjust pH of the solution to 9-10 followed by addition of 300 mg of sodium hydrogensulfite. After stirring for 30 min at room temperature, the reaction mixture was partitioned between dichloromethane and dilute ammonium hydroxide. The aqueous layer was thoroughly extracted with dichloromethane. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness. The residue was separated on a preparative TLC to give (-)-deacetylvindoline 22 (27 mg, 64%) as a colorless powder.
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