반응 #12026

반응 방정식

(4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

benzophenone imine

sodium bicarbonate

sodium tert-butoxide

→

product

수율 94.3%

(4R,9aR)-6-(Benzhydrylidene-amino)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

수율 94.3%

용매

toluene

반응 조건

후처리

1. 1
   온도at reflux for 1 h
2. 2
   추출extracted twice with ethyl acetate
3. 3
   세척The combined organic layers were washed with brine
4. 4
   건조dried over magnesium sulfate
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타The residue was purified by chromatography on silica gel (0.032–0.063 mm) with n-hexane:ethyl acetate (2:1) as eluant

실험 절차

A mixture consisting of 0.20 g (0.54 mmol) (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester, 91 μl (0.54 mmol) benzophenone imine, 73.0 mg (0.76 mmol) sodium tert-butoxide, 5.6 mg (0.01 mmol) tris(dibenzylideneacetone)dipalladium chloroform complex and 10.1 mg (0.02 mmol) R-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene in 3 ml toluene was stirred at reflux for 1 h. The reaction mixture was cooled to room temperature, poured into 10% aqueous sodium bicarbonate solution and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by chromatography on silica gel (0.032–0.063 mm) with n-hexane:ethyl acetate (2:1) as eluant to afford the product as a yellow foam (94.3%).

출처