Reaktion #82779

Reaktionsgleichung

methyl iodide

(4aR)-(10bR)-8-chloro-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

sodium hydroxide

→

product

Ausbeute 142.9%

(4aR) -(10bR)-8-chloro-4-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one

Ausbeute 142.9%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 1-liter flask equipped with a condenser and a stirrer
2. 2
   Sonstigewas begun at ambient temperature
3. 3
   Temperaturgentle heating
4. 4
   TemperaturThe temperature was raised as high as 41°
5. 5
   Sonstigewas then gradually lowered to 29° at the end of 16 hours
6. 6
   workup.STIRRINGof stirring
7. 7
   WaschenHPLC liquid chromatography, eluting with 1:1 acetonitrile
8. 8
   Sonstigehad been consumed
9. 9
   Sonstigethe aqueous layer was removed
10. 10
    EinengenThe organic layer was concentrated to an oil under vacuum
11. 11
    workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
12. 12
    WaschenThe solution was washed with brine
13. 13
    Waschenthe organic layer was washed with 200 mL of water twice
14. 14
    Trocknenwas dried over magnesium sulfate
15. 15
    Sonstigeevaporated under vacuum while heptane
16. 16
    workup.ADDITIONwas added portionwise as the ethyl acetate
17. 17
    Sonstigewas removed
18. 18
    workup.ADDITIONA total of 500 mL of heptane was added
19. 19
    Sonstigeto crystallize when about half of it
20. 20
    workup.ADDITIONhad been added
21. 21
    EinengenThe slurry was concentrated to about 300 ml
22. 22
    Filtrationfiltered
23. 23
    Waschenthe solids were washed with heptane
24. 24
    Sonstigedried in vacuum at 40°-50°

Vorschrift

To a 1-liter flask equipped with a condenser and a stirrer were added 470 mL of THF, 18.7 g of methyl iodide and 47 g of (4aR)-(10bR)-8-chloro-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one, and stirring was begun at ambient temperature. To the mixture was added 100 ml of 50% aqueous sodium hydroxide in one portion, and gentle heating was begun. The temperature was raised as high as 41° and was then gradually lowered to 29° at the end of 16 hours of stirring. HPLC liquid chromatography, eluting with 1:1 acetonitrile:aqueous buffer (5% ammonium acetate) and monitoring at 220 nanometers, then showed that all the starting material had been consumed and the aqueous layer was removed. The organic layer was concentrated to an oil under vacuum, and the residue was dissolved in ethyl acetate. The solution was washed with brine, and the organic layer was washed with 200 mL of water twice, and was dried over magnesium sulfate and evaporated under vacuum while heptane was added portionwise as the ethyl acetate was removed. A total of 500 mL of heptane was added, and the product began to crystallize when about half of it had been added. The slurry was concentrated to about 300 ml, and filtered, and the solids were washed with heptane and dried in vacuum at 40°-50° to obtain 47.03 g of product, m.p. 97°-99°, of 98.7% purity.

Quelle