新产品编号:1531885

Chemical Name: [1-(4,4-diphenyl-3-butenyl)piperidin-3-yl]phosphinic acid
项目整合开发状态: Biological Testing
项目研究机构: Danish University of Pharmaceutical Sci. (Originator)
合成路线:The protection of 3-piperidinol (I) with tert-butoxycarbonyl anhydride or benzyloxycarbonyl chloride gives the corresponding protected piperidine (II),which is oxidized with CrO3 and acetic anhydride in pyridine yielding the piperidinone (III).The condensation of (III) with phosphinate (IV) and triethylamine at 100 C affords the alpha-hydroxyphosphinate (V),which is acylated with methoxalyl chloride (VI) and DMAP giving the methoxalyl ester (VII).The reduction of (VII) with tributyl in hydride and AIBN yields the protected phophinate (VIII),which is finally deprotected and hydrolyzed with 6M HCl.

合成路线:The protection of 3-piperidinol (I) with tert-butoxycarbonyl anhydride or benzyloxycarbonyl chloride gives the corresponding protected piperidine (II),which is oxidized with CrO3 and acetic anhydride in pyridine yielding the piperidinone (III).The condensation of (III) with phosphinate (IV) and triethylamine at 100 C affords the alpha-hydroxyphosphinate (V),which is acylated with methoxalyl chloride (VI) and DMAP giving the methoxalyl ester (VII).The reduction of (VII) with tributyl in hydride and AIBN yields the protected phophinate (VIII),which is deprotected with trifluoroacetic acid affording (IX) with its free NH group.The alkylation of (IX) with 4,4-diphenyl-3-butenyl bromide (X) provides the alkylated piperidinephosphinate (XI),which is finally hydrolyzed with refluxing 6M HCl.