McN-5652Z-药物合成数据库

【药物名称】McN-5652Z

化学结构式(Chemical Structure):

参考文献No.	51629
标题:	McN-5707 and McN-5652-Z
作者:	Gardocki, J.F.; Shank, R.P.; Maryanoff, B.E.
来源:	Drugs Fut 1986,11(1),18

合成路线图解说明: 4-(Methylsulfanyl)mandelic acid and 2-phenylpyrrolidine (I) are heated in refluxing xylene with azeotropic removal of water. The resulting mandelamide (III) is cyclized in polyphosphoric acid at 100 C to a mixture of two diastereomeric lactams. The desired isomer, the minor component (ca- 35%), is separated by preparative HPLC and reduced with borane tetrahydrofuran to the final product. The perchlorate salt crystallizes from 2-propanol on treatment of the free base with the requisite amount of 70% perchloric acid.

参考文献No.	555592
标题:	Pyrroloisoquinoline antidepressants. Potent, enantioselective inhibition of tetrabenazine-induced ptosis and neuronal uptake of norepinephrine, dopamine, and serotonin
作者:	Maryanoff, B.E.; McComsey, D.F.; Castanzo, M.J.; Setler, P.E.; Gardocki, J.F.; Shank, R.P.; Schneider, C.R.
来源:	J Med Chem 1984,27(8),943

合成路线图解说明: 4-(Methylsulfanyl)mandelic acid and 2-phenylpyrrolidine (I) are heated in refluxing xylene with azeotropic removal of water. The resulting mandelamide (III) is cyclized in polyphosphoric acid at 100 C to a mixture of two diastereomeric lactams. The desired isomer, the minor component (ca- 35%), is separated by preparative HPLC and reduced with borane tetrahydrofuran to the final product. The perchlorate salt crystallizes from 2-propanol on treatment of the free base with the requisite amount of 70% perchloric acid.

合成路线图解说明: 2-Chlorostyrene oxide is condensed with 2-phenylpyrrolidine in refluxing ethanol, and the resultant amino alcohol (II) is cyclized in polyphosphoric acid at 100 C to a mixture of two diastereomeric amines. The desired diastereomer, the minor component (ca. 25%), is separated readily by preparative HPLC. The hydrobromide salt crystallizes from 2-propanol on treatment ot the free base with the requisite amount of 48% HBr.