Реакция #44642

Уравнение реакции

(2R,6S)-6-(4-chlorophenyl)piperidine-2-carboxylic acid methyl ester

THF

lithium aluminium hydride

sodium hydroxide

→

title compound

Выход 86.5%

[(2R,6S)-6-(4-chlorophenyl)piperidin-2-yl]methanol

Выход 86.5%

Растворители

ethyl acetate

water

water

Условия реакции

Обработка

1. 1
   ДругоеThe resulting reaction solution
2. 2
   Другоеat −20° C
3. 3
   ДругоеThe resulting reaction solution
4. 4
   workup.STIRRINGwas stirred at room temperature for 15 min
5. 5
   ДругоеThe resulting reaction solution
6. 6
   Фильтрацияwas filtered through Celite
7. 7
   Концентрированиеthe filtrate was concentrated under reduced pressure
8. 8
   ДругоеThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH, eluting solvent: heptane-ethyl acetate system)

Методика

In nitrogen atmosphere, (2R,6S)-6-(4-chlorophenyl)piperidine-2-carboxylic acid methyl ester (2.47 g) was added to a THF suspension (50 mL) of lithium aluminium hydride (508 mg) at −20° C. The resulting reaction solution was stirred at −20° C. for 1 hr, and then water (0.51 mL), a 5 N sodium hydroxide aqueous solution (0.51 mL), and water (1.53 mL) were added thereto in this order at −20° C. The resulting reaction solution was stirred at room temperature for 15 min, and then ethyl acetate was added thereto. The resulting reaction solution was filtered through Celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH, eluting solvent: heptane-ethyl acetate system) to give 1.90 g of the title compound. The physical property values of this compound were as follows:

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