Reaktion #88563

Reaktionsgleichung

lithium tetrahydroaluminate

tert-butyl 1-benzyl-4-methylpiperidine-4-carboxylate

sodium hydroxide

→

title compound

(1-benzyl-4-methylpiperidin-4-yl)methanol

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was then cooled to 0° C.
2. 2
   Sonstigeproducing a white precipitate
3. 3
   FiltrationThe mixture was filtered
4. 4
   Waschenthe solids were washed with ethyl acetate (100 mL)
5. 5
   SonstigeThe combined filtrate was separated
6. 6
   Extraktionthe aqueous portion was extracted with ethyl acetate (2×50 mL)
7. 7
   TrocknenThe combined organic portions were dried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated in vacuo
10. 10
    Sonstigepurified flash chromatography (silica, 80 g, ISCO, 45-100% ethyl acetate in heptane)

Vorschrift

A solution of tert-butyl 1-benzyl-4-methylpiperidine-4-carboxylate (4.7 g, 18 mmol) in diethyl ether (47 mL) was cooled at 0° C. and to this was added lithium tetrahydroaluminate (990 mg, 25 mmol) portion-wise. The reaction mixture was warmed to ambient temperature and stirred vigorously for 1 hour. The mixture was then cooled to 0° C. and a 1N solution of sodium hydroxide (6 mL) was added dropwise to the reaction mixture producing a white precipitate. The mixture was filtered and the solids were washed with ethyl acetate (100 mL). The combined filtrate was separated and the aqueous portion was extracted with ethyl acetate (2×50 mL). The combined organic portions were dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 80 g, ISCO, 45-100% ethyl acetate in heptane) to afford the title compound as a white solid, which was used in the next step without any further purification (2.7 g, 67%).

Quelle