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

Temperature

-20 °C

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:

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

ORD record

ord-215bc8314c444776914eedc2a913ef7b

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07737141B2