benzyl 4-(2-chloroacetyl)-1-piperidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】56084

【品名】benzyl 4-(2-chloroacetyl)-1-piperidinecarboxylate

【CA登记号】

【分子式】C₁₅H₁₈ClNO₃

【分子量】295.76556

【元素组成】C 60.91% H 6.13% Cl 11.99% N 4.74% O 16.23%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV)

N-(Benzyloxycarbonyl)isonipecotic acid (I) was activated as the acid chloride (II) employing oxalyl chloride in the presence of a catalytic amount of DMF. Addition of diazomethane to acid chloride (II) produced the intermediate diazo ketone (III) which, upon treatment with an ethereal solution of HCl, led to the chloromethyl ketone (IV).

参考文献中间体

合成目标

【1】 De Laszlo, S.E.; Mantlo, N.B.; Ponticello, G.S.; Selnick, H.G.; Liverton, N.J. (Merck & Co., Inc.); 2-Substd. aryl pyrroles, compsns. containing such cpds. and methods of use. EP 0863757; JP 1999510510; US 5792778; WO 9705877 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	56082	Z-Isonipecotic acid	10314-98-4	C₁₄H₁₇NO₄	详情	详情
(II)	36165	4,7-dimethoxy-6-[2-(1-piperidinyl)ethoxy]-1-benzofuran-5-amine; 4,7-dimethoxy-6-[2-(1-piperidinyl)ethoxy]-1-benzofuran-5-ylamine		C₁₇H₂₄N₂O₄	详情	详情
(III)	56083	benzyl 4-(2-diazoacetyl)-1-piperidinecarboxylate		C₁₅H₁₇N₃O₃	详情	详情
(IV)	56084	benzyl 4-(2-chloroacetyl)-1-piperidinecarboxylate		C₁₅H₁₈ClNO₃	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

Acylation of the lithium derivative of 4-picoline (VI) with the Weinreb amide of 4-fluorobenzoic acid (V) yielded ketone (VII). The sodium enolate of (VII) was then alkylated with chloro ketone (IV) to afford diketone (VIII). The Paal-Knorr cyclization of diketone (VIII) in the presence of ammonium acetate in boiling HOAc led to pyrrole (IX). Finally, reduction of the benzyloxycarbonyl group of (IX) by means of LiAlH4 furnished the target N-methyl piperidine.

参考文献中间体

合成目标

【1】 De Laszlo, S.E.; Mantlo, N.B.; Ponticello, G.S.; Selnick, H.G.; Liverton, N.J. (Merck & Co., Inc.); 2-Substd. aryl pyrroles, compsns. containing such cpds. and methods of use. EP 0863757; JP 1999510510; US 5792778; WO 9705877 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	56084	benzyl 4-(2-chloroacetyl)-1-piperidinecarboxylate		C₁₅H₁₈ClNO₃	详情	详情
(V)	29514	4-fluoro-N-methoxy-N-methylbenzamide		C₉H₁₀FNO₂	详情	详情
(VI)	31150	4-methylpyridine	108-89-4	C₆H₇N	详情	详情
(VII)	45005	1-(4-fluorophenyl)-2-(4-pyridinyl)-1-ethanone		C₁₃H₁₀FNO	详情	详情
(VIII)	56085	benzyl 4-[4-(4-fluorophenyl)-4-oxo-3-(4-pyridinyl)butanoyl]-1-piperidinecarboxylate		C₂₈H₂₇FN₂O₄	详情	详情
(IX)	56086	benzyl 4-[5-(4-fluorophenyl)-4-(4-pyridinyl)-1H-pyrrol-2-yl]-1-piperidinecarboxylate		C₂₈H₂₆FN₃O₂	详情	详情

Extended Information