Reaktion #5792

Reaktionsgleichung

hydrogen

water

(±)-cis-9-(cyanomethyl)-6,10-dioxaspiro[4.5]decane-7-acetic acid

ammonia

→

(±)-cis-9-(2-aminoethyl)-6,10-dioxaspiro[4.5]decane-7-acetic acid

Ausbeute 47.2%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe suspension is cooled
2. 2
   Filtrationfiltered
3. 3
   Sonstigeto remove the Raney nickel
4. 4
   Filtrationthrough filter aid
5. 5
   Waschenthe precipitate is washed with methanol
6. 6
   EinengenThe filtrate is concentrated at reduced pressure
7. 7
   workup.DISSOLUTIONThe residue is dissolved in methanol saturated with anhydrous ammonia
8. 8
   workup.ADDITIONtreated with decolorizing charcoal
9. 9
   Filtrationfiltered
10. 10
    Filtrationthrough filter aid
11. 11
    Sonstigeevaporated

Vorschrift

A solution of 1.17 g (4.88 mmol) of (±)-cis-9-(cyanomethyl)-6,10-dioxaspiro[4.5]decane-7-acetic acid in 100 mL of methanol saturated with anhydrous ammonia is added to a Parr shaker bottle containing 0.53 g of water wet Raney nickel #30. The solution is heated at 45° C. and 50 pounds per square inch gage (psig) hydrogen pressure for 17 hours. The suspension is cooled and filtered to remove the Raney nickel through filter aid and the precipitate is washed with methanol. The filtrate is concentrated at reduced pressure. The residue is dissolved in methanol saturated with anhydrous ammonia treated with decolorizing charcoal, filtered through filter aid and evaporated to give 0.56 g of (±)-cis-9-(2-aminoethyl)-6,10-dioxaspiro[4.5]decane-7-acetic acid.

Quelle