반응 #57989

반응 방정식

(2-Hydroxyethyl)carbamic acid tert-butyl ester

4-hydroxybenzoic acid methyl ester

diisopropyl azodicarboxylate

Acetyl Chloride

Triphenylphosphine

→

4-(2-aminoethoxy)benzoic acid methyl ester hydrochloride

수율 93.5%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타the reaction temperature below 10° C
2. 2
   workup.ADDITIONAfter addition
3. 3
   온도to warm slowly to ambient temperature
4. 4
   기타After completion of reaction, solvent
5. 5
   workup.DISTILLATIONwas distilled under reduced pressure
6. 6
   workup.DISSOLUTIONthe resulting oil was dissolved in ethanol (500 ml)
7. 7
   기타to rise to 40° C
8. 8
   workup.STIRRINGThe resulting suspension was stirred at 40° C. until completion of reaction
9. 9
   기타After completion of reaction
10. 10
    여과the resulting crystals were filtered on a coarse frit
11. 11
    세척washed with ethyl Acetate (300 mL)
12. 12
    기타The material is dried in vacuo

실험 절차

(2-Hydroxyethyl)carbamic acid tert-butyl ester (152.0 g, 0.942 mol) and 4-hydroxybenzoic acid methyl ester (174.0 g, 1.12 mol) were dissolved in tetrahydrofuran (2000 ml) and cooled to 0-5° C. Triphenylphosphine (292.8 g 1.116 mol) was added to the cooled mixture. A solution of diisopropyl azodicarboxylate (246.0 g, 1.218 mol) in tetrahydrofuran (400 ml) was added dropwise over a period of one to two hours keeping the reaction temperature below 10° C. After addition, the reaction was allowed to warm slowly to ambient temperature and stirred overnight. After completion of reaction, solvent was distilled under reduced pressure and the resulting oil was dissolved in ethanol (500 ml) and ethyl acetate (2000 ml). Acetyl Chloride (222.0 g, 2.826 mol) was added drop wise over fifteen minutes with the temperature allowed to rise to 40° C. The resulting suspension was stirred at 40° C. until completion of reaction. After completion of reaction, the resulting crystals were filtered on a coarse frit and washed with ethyl Acetate (300 mL). The material is dried in vacuo to give of 4-(2-aminoethoxy)benzoic acid methyl ester hydrochloride (204.1 g) as a white crystalline solid.

출처