반응 #1620

반응 방정식

potassium carbonate

diethyl dibromomalonate

(R)-2-(3,4-dihydroxyphenyl)propylcarbamic acid, t-butyl ester

→

(R)-5-[N-(t-Butyloxycarbonyl)-2-aminopropyl]-1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester

용매

acetone

acetone

반응 조건

후처리

1. 1
   온도After cooling to ambient temperature
2. 2
   workup.STIRRINGthe reaction was stirred at ambient temperature for 18 hours
3. 3
   여과The suspension was filtered
4. 4
   세척the residue was washed with ethyl acetate
5. 5
   기타evaporated
6. 6
   기타the residue was partitioned between ethyl acetate (200 ml) and dilute hydrochloric acid (100 ml, pH5)
7. 7
   기타The organic layer was separated
8. 8
   세척washed with water (2×100 ml) and brine (100 ml)
9. 9
   건조dried (MgSO4)
10. 10
    기타evaporated
11. 11
    기타The residue was purified by column chromatography on silica gel eluting with 25% ethyl acetate in n-hexane giving the title compound as an oil

실험 절차

A solution of (R)-2-(3,4-dihydroxyphenyl)propylcarbamic acid, t-butyl ester. (1.07 g, 4 mMol) in acetone (25 ml) containing potassium carbonate (3 equiv, 1.66 g, 12 mMol) was stirred at 60° C. under an argon atmosphere for 1 hour. After cooling to ambient temperature, a solution of diethyl dibromomalonate (1.27 g, 4 mMol) in acetone (7 ml) was added and the reaction was stirred at ambient temperature for 18 hours. The suspension was filtered and the residue was washed with ethyl acetate. The filtrates were combined, evaporated and the residue was partitioned between ethyl acetate (200 ml) and dilute hydrochloric acid (100 ml, pH5). The organic layer was separated, washed with water (2×100 ml) and brine (100 ml), dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel eluting with 25% ethyl acetate in n-hexane giving the title compound as an oil;

출처