반응 #83619

반응 방정식

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

수율 98.1%

용매

hexane

tetrahydrofuran

반응 조건

후처리

1. 1
   온도to warm to -20° C
2. 2
   추출The mixture was extracted once with diethyl ether
3. 3
   workup.ADDITIONwith the addition of cold 5N sodium hydroxide solution
4. 4
   추출The basic mixture was extracted twice with methylene chloride
5. 5
   세척The combined organic solution was washed with a saturated sodium chloride solution
6. 6
   건조The methylene chloride solution was dried over magnesium sulfate
7. 7
   기타evaporated

실험 절차

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.

출처