반응 #12016

반응 방정식

potassium sodium tartrate

ethyl acetate

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

lithium aluminium hydride

→

compound

수율 50.5%

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

수율 50.5%

용매

diethyl ether

반응 조건

후처리

1. 1
   여과then filtered through a short pad of dicalite speed plus
2. 2
   추출The aqueous phase was extracted four times 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 ethyl acetate

실험 절차

To a solution of 245.0 mg (0.63 mmol) (4R,9aR)-6-(2-ethoxycarbonyl-vinyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 12, intermediate) in 10 ml diethyl ether were added 50.0 mg (1.32 mmol) lithium aluminium hydride. After 2 h the reaction mixture was poured into saturated aqueous potassium sodium tartrate solution and ethyl acetate then filtered through a short pad of dicalite speed plus. The aqueous phase was extracted four times with ethyl acetate and 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 ethyl acetate:n-hexane as eluant to afford the compound as a colorless solid (50.5%).

출처