反応 #1166423

反応方程式

ethanolamine

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

triphenyl phosphine

sodium hydroxide

allylbenzene

9-BBN

→

title compound

収率 59.0%

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

収率 59.0%

溶媒

ethyl acetate

THF

THF

THF

反応条件

後処理

1. 1
   その他at 0°
2. 2
   温度warming to 5°
3. 3
   温度The resulting mixture was heated at 80° for 18 h
4. 4
   温度cooled
5. 5
   洗浄The resulting organic phase was washed with brine
6. 6
   乾燥dried over sodium sulfate
7. 7
   濃縮concentrated
8. 8
   その他purified by silica gel chromatography (50-100% ethyl acetate/hexanes eluent gradient)

実験手順

To a solution of allylbenzene (106 mg, 0.89 mmol) in 0.5 mL of THF was added 9-BBN (0.89 mmol, 1 eguiv) in THF, at 0°. Let stir for 1 h, warming to 5°. To the mixture was added (+)-(4aR)-(10bR)-8-bromo-10b-methyl-1,2,3,4,4a,5,6,10b-octahydrobenzo[f]quinolin-3-one (250 mg, 0.812 mmol), triphenyl phosphine (42 mg, 0.16 equiv.), tetrakis(triphenylphosphine) palladium(0) (19 mg, 0.02 equiv.), 1 mL of 3N sodium hydroxide solution and an additional 1 mL of THF. The resulting mixture was heated at 80° for 18 h, cooled, and ethanolamine was added, followed by ethyl acetate. The resulting organic phase was washed with brine, dried over sodium sulfate, concentrated, and purified by silica gel chromatography (50-100% ethyl acetate/hexanes eluent gradient) to give 160 mg (59%) of the title compound as an oil. FDMS m/e=347.

出典