反応 #1166322

反応方程式

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

phenylboronic acid

sodium carbonate

toluene

→

title compound

収率 70.0%

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

収率 70.0%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他fitted with a reflux condenser
2. 2
   温度the stirred mixture was heated at 80°, under nitrogen, for 24 h
3. 3
   温度The mixture was cooled
4. 4
   洗浄washed with brine (2×25 mL)
5. 5
   乾燥The combined organic extracts were dried over sodium sulfate
6. 6
   濃縮concentrated
7. 7
   その他purified by silica gel chromatography (ethyl acetate eluent)
8. 8
   その他followed by recrystallization from ethyl acetate

実験手順

A 15 mL round bottom flask was charged with (+)-(4aR)-(10bR)-4-methyl-8-bromo-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (200 mg, 0.65 mmol), tetrakis (triphenylphosphine) palladium (0) (23mg, 0.02 mmol), phenylboronic acid (95 mg, 0.78 mmol) ,0.65 mL of 2M sodium carbonate solution and 2 mL of toluene, fitted with a reflux condenser, and the stirred mixture was heated at 80°, under nitrogen, for 24 h. The mixture was cooled, diluted with dichloromethane (75 mL) and washed with brine (2×25 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (ethyl acetate eluent), followed by recrystallization from ethyl acetate, to give 139 mg (70%) of the title compound as a white solid. mp 155°. FDMS: m/e=305.

出典