반응 #217684

반응 방정식

trimethylphosphine tetrahydrofuran

(1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfanyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

sodium hydrogen carbonate

→

(1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfanyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

수율 87.8%

용매

tetrahydrofuran

water

diethyl ether

반응 조건

후처리

1. 1
   기타After separation
2. 2
   세척the organic layers were washed with a saturated aqueous solution of sodium chloride
3. 3
   건조dried over anhydrous sodium sulfate
4. 4
   여과The desiccant was filtered off
5. 5
   농축the filtrate was concentrated under reduced pressure
6. 6
   workup.ADDITIONThe residue was diluted with chloroform
7. 7
   workup.ADDITIONsilica gel (Wako gel C200 (made by Wako Pharmaceutical Industries Ltd.)) was added
8. 8
   농축The mixture was concentrated under reduced pressure
9. 9
   workup.WAITleft
10. 10
    workup.WAITto stand for 18 hours at room temperature
11. 11
    기타purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=2:1)

실험 절차

7.7 mL of a solution of 1M trimethylphosphine/tetrahydrofuran was added to 3.35 g of (1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfanyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester dissolved in 100 mL of tetrahydrofuran and 10 mL of water, and the mixture was stirred for 1 hour at room temperature. The mixture was diluted with 200 mL of diethyl ether, and after 50 mL of a saturated aqueous solution of sodium hydrogen carbonate was added thereto, the mixture was stirred for 1.5 hours at room temperature. After separation, the organic layers were washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The residue was diluted with chloroform, and then silica gel (Wako gel C200 (made by Wako Pharmaceutical Industries Ltd.)) was added thereto. The mixture was concentrated under reduced pressure, left to stand for 18 hours at room temperature, and then purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=2:1), thereby yielding 2.78 g of (1R,2S,3R,5R,6R)-2-amino-3-(3,4-dichlorobenzylsulfanyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

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