Reaktion #2042363

Reaktionsgleichung

4-benzyl-1-(2-(3-(ethoxycarbonylmethyl)phenoxy)ethyl)piperidine

Water

NaOH

water

lithium aluminum hydride

→

title product

Ausbeute 66.0%

4-Benzyl-1-(2-(3-(2-hydroxyethyl)phenoxy) ethyl)piperidine

Ausbeute 66.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe colorless solid was removed by filtration
2. 2
   Waschenwashed with EtOAc (3×20 mL)
3. 3
   TrocknenThe filtrate was dried over Na2SO4
4. 4
   SonstigeEvaporation of solvents
5. 5
   Sonstigegave a residue, which
6. 6
   Sonstigewas purified by flash chromatography

Vorschrift

To a suspension of lithium aluminum hydride (150 mg, 4.0 mmol) in 10 mL of anhydrous THF was added dropwise a solution of 4-benzyl-1-(2-(3-(ethoxycarbonylmethyl)phenoxy)ethyl)piperidine (0.382 g, 1.00 mmol) in 2 mL of THF at -78° C. The resulting mixture was allowed to warm to room temperature and was stirred for 12 hr. Water (0.2 mL), 15% NaOH aqueous solution (0.2 mL) and water (1 mL) were added successively. The colorless solid was removed by filtration and washed with EtOAc (3×20 mL). The filtrate was dried over Na2SO4. Evaporation of solvents gave a residue, which was purified by flash chromatography giving the title product as colorless oil (223 mg, 66%) 1H NMR (CDCl3) 1.37 (m, 2 H), 1.60 (m, 1 H), 1.63 (m, 2 H), 2.05 (m, 2 H), 2.36 (d, J=6.6 Hz, 2 H), 2.76 (m, 2 H), 2.82 (m, 2 H), 2.95 (m, 3 H), 3.81 (t, J=6.9 Hz, 2 H), 4.08 (t, J=6.9 Hz, 2 H), 6.80 (m, 3 H), 7.17-7.29 (m, 6 H).

Quelle