反応 #83619

反応方程式

hydrochloric acid

n-butyllithium

(+)(2aR,4S)-1-benzoyl-6-bromo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole

→

(-)(2aR,4S)-6-bromo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole

収率 98.1%

溶媒

hexane

tetrahydrofuran

反応条件

後処理

1. 1
   温度to warm to -20° C
2. 2
   抽出The mixture was extracted once with diethyl ether
3. 3
   workup.ADDITIONwith the addition of cold 5N sodium hydroxide solution
4. 4
   抽出The basic mixture was extracted twice with methylene chloride
5. 5
   洗浄The combined organic solution was washed with a saturated sodium chloride solution
6. 6
   乾燥The methylene chloride solution was dried over magnesium sulfate
7. 7
   その他evaporated

実験手順

To a stirred solution of 12.8 g (29 mmol) of (+)(2aR,4S)-1-benzoyl-6-bromo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole in 200 ml of tetrahydrofuran cooled to -78° C. under a nitrogen atmosphere was added 20 ml (32 mmol) of a 1.6M solution of n-butyllithium in hexane. The reaction mixture was stirred at -78° C. for 30 minutes and then allowed to warm to -20° C. To the reaction mixture was added 50 ml of a 1N hydrochloric acid solution. The mixture was extracted once with diethyl ether. The acidic solution was made alkaline with the addition of cold 5N sodium hydroxide solution. The basic mixture was extracted twice with methylene chloride. The combined organic solution was washed with a saturated sodium chloride solution. The methylene chloride solution was dried over magnesium sulfate and evaporated to give 9.6 g of (-)(2aR,4S)-6-bromo-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole.

出典