Reaktion #82787

Reaktionsgleichung

propyl iodide

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

→

white crystalline product

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

Lösungsmittel

sodium hydroxide

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated to about 60°
2. 2
   Sonstigeby separating the organic layer
3. 3
   Sonstigeevaporating it to dryness
4. 4
   workup.ADDITIONadding water and ethyl acetate
5. 5
   SonstigeThe organic layer was separated
6. 6
   Waschenwashed twice with water
7. 7
   Sonstigedried
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated under vacuum

Vorschrift

A 2.35 g portion of (4aR)-(10bR)-8-chloro-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one was slurried in 40 mL of THF and 5 mL of 50% aqueous sodium hydroxide, and 3.4 g of propyl iodide was added. The mixture was heated to about 60°, and the mixture was stirred at that temperature for about 22 hours. Workup was carried out by separating the organic layer and evaporating it to dryness, and adding water and ethyl acetate. The organic layer was separated, washed twice with water, dried, filtered and evaporated under vacuum to obtain 710 mg of white crystalline product, found to be of about 90% purity. It was then purified by silica gel flash chromatography, eluting with ethyl acetate, to obtain 510 mg of purified product, m.p. 110°-11° of 98.98% purity, by HPLC eluting with 1:1 acetonitrile:aqueous buffer (5% ammonium acetate) and monitoring at 220 nanometers.

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