合成路线:Trapencaine is prepared from 3-(n-pentyloxy)phenylisocyanate and (+)-trans-2-(1-pyrrolidinyl)cyclohexanol in dry benzene or some other inert solvent.Stereochemically pure isomer is obtained by treatment of the pure base with hydrochloric acid,yielding the corresponding salt.
合成路线:By refluxing a solution of equimolecular quantities of 3-pentyloxyphenyl isocyanate (I) and trans-2-(1-pyrrolidinyl)cyclohexanol (II) in toluene.The obtained pentacaine base is transformed to the hydrochloride by treatment of an ether solution of anhydrous hydrogen chloride (1,2).The starting amino-alcohol (II) is prepared from cyclohexanol (III),which is first dehydrated to cyclohexene (IV).The following addition of HClO gives trans-2-chlorocyclohexanol (V),which,in turn is dehydrochlorinated to 1,2-epoxycyclohexane (VI).Final addition of pyrrolidine (A) yields the required intermediate (II).
参考文献标题:Alkoxycarbanilic acid esters with high local anaesthetic activity
文献作者:Benes,L.; Borovansky,A.; Kop醕ov? L.
参考来源:Arzneim-Forsch Drug Res 1969,191902-3
合成路线:By refluxing a solution of equimolecular quantities of 3-pentyloxyphenyl isocyanate (I) and trans-2-(1-pyrrolidinyl)cyclohexanol (II) in toluene.The obtained pentacaine base is transformed to the hydrochloride by treatment of an ether solution of anhydrous hydrogen chloride (1,2).The starting amino-alcohol (II) is prepared from cyclohexanol (III),which is first dehydrated to cyclohexene (IV).The following addition of HClO gives trans-2-chlorocyclohexanol (V),which,in turn is dehydrochlorinated to 1,2-epoxycyclohexane (VI).Final addition of pyrrolidine (A) yields the required intermediate (II).
参考文献标题:Basische trans- und cis-Cyklohexylester substituierter Alkoxycarbanils鋟ren.XLI.Studien 黚er Lokalan鋝thetika
文献作者:Benes,L.; Borovansky,A.; Kop醕ov? L.
参考来源:Arch Pharm 1972,305648
合成路线:By refluxing a solution of equimolecular quantities of 3-pentyloxyphenyl isocyanate (I) and trans-2-(1-pyrrolidinyl)cyclohexanol (II) in toluene.The obtained pentacaine base is transformed to the hydrochloride by treatment of an ether solution of anhydrous hydrogen chloride (1,2).The starting amino-alcohol (II) is prepared from cyclohexanol (III),which is first dehydrated to cyclohexene (IV).The following addition of HClO gives trans-2-chlorocyclohexanol (V),which,in turn is dehydrochlorinated to 1,2-epoxycyclohexane (VI).Final addition of pyrrolidine (A) yields the required intermediate (II).
参考文献标题:Pentacaine
文献作者:Castar,J.
参考来源:Drugs Fut 1976,1(8),379
合成路线:By refluxing a solution of equimolecular quantities of 3-pentyloxyphenyl isocyanate (I) and trans-2-(1-pyrrolidinyl)cyclohexanol (II) in toluene.The obtained pentacaine base is transformed to the hydrochloride by treatment of an ether solution of anhydrous hydrogen chloride (1,2).The starting amino-alcohol (II) is prepared from cyclohexanol (III),which is first dehydrated to cyclohexene (IV).The following addition of HClO gives trans-2-chlorocyclohexanol (V),which,in turn is dehydrochlorinated to 1,2-epoxycyclohexane (VI).Final addition of pyrrolidine (A) yields the required intermediate (II).
参考文献标题:Studies on local anesthetics.XLVIII.Preliminary analytical evaluation of the substance K-1902 (pentacaine)
文献作者:Subert,J.; et al.
参考来源:Cesk Farm 1975,245
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