Reaktion #82400

Reaktionsgleichung

sodium hydroxide

5,6-Dimethoxy-3-phenyl-1,2,3,4-tetrahydronaphthalen-1-one

trimethylsilylcyanide

lithium aluminum hydride

→

title compound

Ausbeute 73.4%

1-Aminomethyl-5,6-dimethoxy-1-hydroxy-3-phenyl-1,2,3,4-tetrahydronaphthalene

Ausbeute 73.4%

Lösungsmittel

acetonitrile

diethyl ether

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturat reflux temperature for 2.5 h
3. 3
   TemperaturThe reaction mixture was cooled
4. 4
   Einengenconcentrated
5. 5
   TemperaturAfter the reaction mixture was heated
6. 6
   Temperaturat reflux temperature for 2.5 h
7. 7
   Sonstigeformed
8. 8
   FiltrationThe solid was filtered
9. 9
   Waschenwashed with 3×80 mL of methylene chloride
10. 10
    EinengenThe filtrate was concentrated
11. 11
    Sonstigethe resultant solid was triturated with ethyl acetate/hexane

Vorschrift

5,6-Dimethoxy-3-phenyl-1,2,3,4-tetrahydronaphthalen-1-one (14.6 g, 51.7 mmol), from Example 1, 24 mL of acetonitrile, 10.3 g (104 mmol) of trimethylsilylcyanide, commercially available from Aldrich Chemical Company, and 100 mg of aluminum chloride were mixed together and heated at reflux temperature for 2.5 h. The reaction mixture was cooled and concentrated. The residue was added dropwise to a solution of 4.3 g (113 mmol) of lithium aluminum hydride in 101 mL of diethyl ether. After the reaction mixture was heated at reflux temperature for 2.5 h, 4.3 mL of water was added dropwise, followed by 4.3 mL of 15% aqueous sodium hydroxide solution, followed by a second 4.3 mL of water. The reaction mixture was stirred until a granular precipitate formed. The solid was filtered and washed with 3×80 mL of methylene chloride. The filtrate was concentrated and the resultant solid was triturated with ethyl acetate/hexane to give 11.9 g (73% yield) of the title compound, m.p. 175°-176° C.; 1H NMR (d6 -DMSO) δ: 2.03 (t, 1H), 2.28 (dt, 1H), 2.65 (dd, 1H), 2.83 (dd, 1H), 2.95-3.1 (m, 2H), 3.28 (dd, 1H), 3.75 (s, 3H), 3.86 (s, 3H), 6.87 (d, 1H), 7.2-7.4 (m, 6H).

Quelle