合成路线:Reaction of cyclohexenone (I) with ethyl cyanoacetate (A) in the presence of ammonia affords the Guareschi salt (II),which is hydrolyzed and decarboxylated to give 1,1-cyclohexanediacetic acid (III).The anhydride (IV) can be treated either with methanol to yield the halfester (V),or with hydroxylamine to afford the N-hydroxyimide (VII).The halfester (V) is subjected to a Curtius type rearrangement to give the isocyanate (VI),which is hydrolyzed to the amino acid hydrochloride (Xl).
合成路线:The same product can be obtained from reaction of cyclohexenone (I) with ethyl cyanoacetate (A) in the presence of ammonia affords the Guareschi salt (II),which is hydrolyzed and decarboxylated to give 1,1-cyclohexanediacetic acid (III).The anhydride (IV) can be treated with the N-hydroxyimide (VII) via a Lossen type rearrangement by conversion of (VII) to N-benzenesulfonyloxylmide (VIII) and subsequent reaction with triethylamine in methanol followed by hydrolysis of the urethanester (IX).The free amino acid is finally obtained from the hydrochloride (X) via anion exchange.
参考文献标题:Cyclic sulphonyloxyimides
文献作者:Satzinger,G.; Hartenstein,J.(Pfizer Inc.)
参考来源:DE 2611690; ES 457050; FR 2344540; GB 1575709; JP 52113977; US 4152326
合成路线:Reaction of cyclohexenone (I) with ethyl cyanoacetate (A) in the presence of ammonia affords the Guareschi salt (II),which is hydrolyzed and decarboxylated to give 1,1-cyclohexanediacetic acid (III).The anhydride (IV) can be treated either with methanol to yield the halfester (V),or with hydroxylamine to afford the N-hydroxyimide (VII).The halfester (V) is subjected to a Curtius type rearrangement to give the isocyanate (VI),which is hydrolyzed to the amino acid hydrochloride (Xl).
合成路线:The same product can be obtained from reaction of cyclohexenone (I) with ethyl cyanoacetate (A) in the presence of ammonia affords the Guareschi salt (II),which is hydrolyzed and decarboxylated to give 1,1-cyclohexanediacetic acid (III).The anhydride (IV) can be treated with the N-hydroxyimide (VII) via a Lossen type rearrangement by conversion of (VII) to N-benzenesulfonyloxylmide (VIII) and subsequent reaction with triethylamine in methanol followed by hydrolysis of the urethanester (IX).The free amino acid is finally obtained from the hydrochloride (X) via anion exchange.
参考文献标题:Gabapentin
文献作者:Castar,J.; Serradell,M.N.
参考来源:Drugs Fut 1984,9(6),418
产品链接: CAS No. 60142-96-3››