Reaktion #54344

Reaktionsgleichung

tetrahydrofuran

1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1,2,5,6-tetrahydropyridine

sodium borohydride

tetrahydrofuran

→

title compound

1-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo a mixture of 39.9 g
2. 2
   TemperaturThe reaction mixture is cooled in ice
3. 3
   Sonstigequenched with 6.5 ml
4. 4
   workup.ADDITIONof 30% hydrogen peroxide are added dropwise
5. 5
   workup.STIRRINGAfter several minutes stirring the reaction
6. 6
   Temperaturis cooled
7. 7
   workup.ADDITIONof concentrated hydrochloric acid is added dropwise
8. 8
   SonstigeThe reaction mixture is partially evaporated
9. 9
   ExtraktionThe concentrated mixture is extracted with 250 ml
10. 10
    Extraktionof ether, the ether extract
11. 11
    Waschenwashed with 100 ml
12. 12
    Trocknenof saturated sodium chloride, dried over magnesium sulfate
13. 13
    Sonstigeevaporated
14. 14
    SonstigeThe residue is purified via column chromatography on 400 g
15. 15
    Waschenof silica gel eluted with 50% ether-cyclohexane

Vorschrift

To a mixture of 39.9 g. (80 mmols.) of 1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-1,2,5,6-tetrahydropyridine and 4.8 g. (115 mmols.) of sodium borohydride in 50 ml. of tetrahydrofuran is added 21.6 ml. (180 mmols.) of borontrifluoride etherate complex in 40 ml. of tetrahydrofuran during a 2 hour period at 0°-5° C. Stirring is continued 2 hours longer at 25° C. The reaction mixture is cooled in ice and quenched with 6.5 ml. of water and then 20 ml. of 2N sodium hydroxide and 20 ml. of 30% hydrogen peroxide are added dropwise. After several minutes stirring the reaction is cooled and 20 ml. of concentrated hydrochloric acid is added dropwise. The reaction mixture is partially evaporated and then made basic with 6N sodium hydroxide. The concentrated mixture is extracted with 250 ml. of ether, the ether extract washed with 100 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 400 g. of silica gel eluted with 50% ether-cyclohexane to yield the title compound.

Quelle