Reaktion #962446

Reaktionsgleichung

Benzyl piperazine

compound

((5aR,9bS)-3,3a-Dihydroxy-5a,9-dimethyl-2-oxo-2,3,3a,4,5,5a,6,7,8,9b-decahydronaphtho[1,2-b]furan-3-yl)methyl 4-methylbenzenesulfonate

→

title compound

(5aR,9bS)-3-((4-Benzylpiperazin-1-yl)methyl)-3,3a-dihydroxy-5a,9-dimethyl-3,3a,4,5,5a,6,7,8-octahydronaphtho[1,2-b]furan-2(9bH)-one

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated
2. 2
   workup.DISSOLUTIONdissolved in water (25 mL)
3. 3
   Extraktionwas extracted
4. 4
   WaschenEthyl acetate layer was washed with water and brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   SonstigeSolvent was removed
7. 7
   Sonstigecrude product was purified by column chromatography (silica gel, using 12.5% ethyl acetate in petroleum ether)
8. 8
   SonstigeSemi-pure product was crystallized

Vorschrift

Benzyl piperazine (190 mg, 1.078 mmol) was added to the solution of compound of example 5 (470 mg, 1.078 mmol) in ethanol (15 mL), and stirred at 50° C. under nitrogen atmosphere for 6 hours. The reaction mixture was concentrated, and dissolved in water (25 mL) and was extracted using ethyl acetate (3×50 mL). Ethyl acetate layer was washed with water and brine, dried over sodium sulfate. Solvent was removed and crude product was purified by column chromatography (silica gel, using 12.5% ethyl acetate in petroleum ether). Semi-pure product was crystallized using ethyl acetate/petroleum ether to obtain the title compound.

Quelle