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【结 构 式】

【分子编号】26970

【品名】tert-butyl 3-[(diethoxymethyl)(ethoxy)phosphoryl]-3-hydroxy-1-piperidinecarboxylate

【CA登记号】

【 分 子 式 】C17H34NO7P

【 分 子 量 】395.433262

【元素组成】C 51.64% H 8.67% N 3.54% O 28.32% P 7.83%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(Vb)

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

合成路线2

该中间体在本合成路线中的序号:(Vb)

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.

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
(IX) 27066 1-(4,4-diphenyl-3-butenyl)-3-piperidinylphosphinic acid C21H26NO2P 详情 详情
(X) 24116 1-(4-bromo-1-phenyl-1-butenyl)benzene C16H15Br 详情 详情
(XI) 27067 ethyl 1-(4,4-diphenyl-3-butenyl)-3-piperidinylphosphinate C23H30NO2P 详情 详情
Extended Information