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【结 构 式】

【药物名称】

【化学名称】(Piperidin-3-yl)phosphinic acid

【CA登记号】

【 分 子 式 】C5H12NO2P

【 分 子 量 】149.13069

【开发单位】Danish University of Pharmaceutical Sci. (Originator)

【药理作用】GABA Reuptake Inhibitors

合成路线1

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.

1 Stensbol, T.B.; Kehler, J.; Krogsgaard-Larsen, P.; Piperidinyl-3-phosphinic acids as novel uptake inhibitors of the neurotransmitter gamma-aminobutyric acid (GABA). Bioorg Med Chem Lett 1999, 9, 6, 811.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
(IIa) 26964 benzyl 3-hydroxy-1-piperidinecarboxylate C13H17NO3 详情 详情
(IIb) 26965 tert-butyl 3-hydroxy-1-piperidinecarboxylate C10H19NO3 详情 详情
(IIIa) 26966 benzyl 3-oxo-1-piperidinecarboxylate C13H15NO3 详情 详情
(IIIb) 26967 1-N-Boc-3-piperodone; tert-butyl 3-oxo-1-piperidinecarboxylate 98977-36-7 C10H17NO3 详情 详情
(Va) 26969 benzyl 3-[(diethoxymethyl)(ethoxy)phosphoryl]-3-hydroxy-1-piperidinecarboxylate C20H32NO7P 详情 详情
(Vb) 26970 tert-butyl 3-[(diethoxymethyl)(ethoxy)phosphoryl]-3-hydroxy-1-piperidinecarboxylate C17H34NO7P 详情 详情
(VIIa) 26972 benzyl 3-[(diethoxymethyl)(ethoxy)phosphoryl]-3-[(2-methoxy-2-oxoacetyl)oxy]-1-piperidinecarboxylate C23H34NO10P 详情 详情
(VIIb) 26973 tert-butyl 3-[(diethoxymethyl)(ethoxy)phosphoryl]-3-[(2-methoxy-2-oxoacetyl)oxy]-1-piperidinecarboxylate C20H36NO10P 详情 详情
(VIIIa) 26974 benzyl 3-[(diethoxymethyl)(ethoxy)phosphoryl]-1-piperidinecarboxylate C20H32NO6P 详情 详情
(VIIIb) 26975 tert-butyl 3-[(diethoxymethyl)(ethoxy)phosphoryl]-1-piperidinecarboxylate C17H34NO6P 详情 详情
(I) 24255 3-piperidinol 6859-99-0 C5H11NO 详情 详情
(IV) 26968 ethyl diethoxymethylphosphinate C7H17O4P 详情 详情
(VI) 26971 2-methoxy-2-oxoacetyl chloride 5781-53-3 C3H3ClO3 详情 详情
Extended Information