Reaktion #2335306

Reaktionsgleichung

6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-8H-pyrrolo[2,3-i][3]benzazocine

diisopropylethyl amine

4-bromo-2-methyl-2-butene

water

→

product

Ausbeute 35.0%

6,12-Dimethyl-1,2,3,4,5,6-hexahydro-3-(3-methyl-2-butenyl)-2,6-methano-8H-pyrrolo-[2,3-i][3]benzazocine

Ausbeute 35.0%

Lösungsmittel

dimethylformamide

dimethylformamide

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe layers were separated
2. 2
   Extraktionthe aqueous layer was extracted with ethyl acetate and ether
3. 3
   WaschenThe combined organic layers were washed with brine
4. 4
   Trocknendried over anhydrous potassium carbonate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate)

Vorschrift

To a stirred solution of 1.42 g of 6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-8H-pyrrolo[2,3-i][3]benzazocine and 40 ml of dimethylformamide was added 1.54 ml of diisopropylethyl amine. The mixture was cooled to 0° C. and 0.97 g of 4-bromo-2-methyl-2-butene in 8 ml of dimethylformamide was added, under nitrogen. The mixture was stirred at 0° C. for an additional 1.25 hr, and was poured into water and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate and ether. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate, filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 2% triethylamine/ethyl acetate) to afford 0.63 g (35%) of product, mp 62°-65° C.

Quelle