2,3-(Methylenedioxy)benzaldehyde; 1,3-Benzodioxole-4-carbaldehyde -Drug Synthesis Database

【结构式】

【分子编号】13329

【品名】2,3-(Methylenedioxy)benzaldehyde; 1,3-Benzodioxole-4-carbaldehyde

【CA登记号】7797-83-3

【分子式】C₈H₆O₃

【分子量】150.13384

【元素组成】C 64% H 4.03% O 31.97%

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：(II)

The cyclization of 2,3-dihydroxybenzaldehyde (I) with dibromomethane by means of KF in hot DMF gives 2,3-methylenedioxybenzaldehyde (II), which is condensed with ethyl acetoacetate (III) by means of piperidine and acetic acid in refluxing benzene to afford ethyl 2-acetyl-3-(2,3-methylenedioxyphenyl)acrylate (IV). Finally, this compound is cyclized with methyl 3-aminocrotonate (V) in hot isopropanol.

参考文献中间体

合成目标

【1】 Galiano Ramos, J.A.; Verde Casanova, M.J. (IIDQB (Madrid); Laboratoires Delagrange); Calcium antagonists. BE 0902016; CH 663020; DE 3510762; EP 0158211; FR 2562069; GB 2156809; JP 1985248671; US 4722931 .
【2】 Serradell, M.N.; Castaner, J.; Castaner, R.M.; Oxodipine. Drugs Fut 1987, 12, 7, 633.

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)	12380	2,3-Dihydroxybenzaldehyde	24677-78-9	C₇H₆O₃	详情	详情
(II)	13329	2,3-(Methylenedioxy)benzaldehyde; 1,3-Benzodioxole-4-carbaldehyde	7797-83-3	C₈H₆O₃	详情	详情
(III)	11819	ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate	141-97-9	C₆H₁₀O₃	详情	详情
(IV)	28848	ethyl 2-(1,3-benzodioxol-4-ylmethyl)-3-oxobutanoate		C₁₄H₁₆O₅	详情	详情
(V)	11372	Methyl (E)-3-amino-2-butenoate; Methyl 3-aminocrotonate		C₅H₉NO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(VI)

Elgodipine can be obtained in three main steps: The alkylation of N-methyl-2-aminoethanol (I) with 4-fluorobenzyl chloride (II) gives 2-[N-(4-fluorobenzyl)-N-methylamino]ethanol (III), which is esterified with 2,2,6-trimethyl-4H-1,3-dioxin-4-one (IV) yielding the corresponding acetoacetic ester (V). The condensation of (V) with 2,3-methylenedioxybenzaldehyde (VI) affords 2-[N-(4-fluorobenzyl)-N-methylamino]ethyl 2-(2,3-methylenedioxybenzylidene]acetoacetate (VII), which is finally cyclized with isopropyl 3-aminocrotonate (VIII). The intermediate aldehyde (VI) is obtained starting from 2,3-dimethoxybenzaldehyde (X), which by demethylation with HCl or HBr yields 2,3-dihydroxybenzaldehyde (XI). Finally, this compound is converted into (VI) in the usual way. The intermediate crotonate (VIII) is obtained by reaction of isopropyl acetoacetate (IX) with ammonia.

参考文献中间体

合成目标

【1】 Galiano, A.; Elgodipine Hydrochloride. Drugs Fut 1995, 20, 3, 231.
【2】 Fernandez Torija, C.; Galiano Ramos, J.A. (IIDQB (Madrid)); 1,4-Dihydropyridines, process for their preparation and their use as medicaments. AU 8820330; BE 1001055; CH 675999; EP 0302980; GB 2208861; JP 1989294675; US 4952592 .
【3】 Serradell, M.N.; Castaner, J.; Castaner, R.M.; Oxodipine. Drugs Fut 1987, 12, 7, 633.

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)	13324	2-Methylaminoethanol; 2-(Methylamino)-1-ethanol	109-83-1	C₃H₉NO	详情	详情
(II)	12354	4-Fluorobenzyl chloride; 1-(Chloromethyl)-4-fluorobenzene	352-11-4	C₇H₆ClF	详情	详情
(III)	13333	2-[(4-Fluorobenzyl)(methyl)amino]-1-ethanol		C₁₀H₁₄FNO	详情	详情
(IV)	13327	2,2,6-Trimethyl-4H-1,3-dioxin-4-one；2,2,6-trimethyl-1,3-dioxin-4-one；2,2,6-trimethyl-m-Dioxin-4-one;3-(1-hydroxy-1-methylethoxy)-d-lactone Crotonicacid	5394-63-8	C₇H₁₀O₃	详情	详情
(V)	13328	2-[(4-fluorobenzyl)(methyl)amino]ethyl 3-oxobutanoate		C₁₄H₁₈FNO₃	详情	详情
(VI)	13329	2,3-(Methylenedioxy)benzaldehyde; 1,3-Benzodioxole-4-carbaldehyde	7797-83-3	C₈H₆O₃	详情	详情
(VII)	13330	2-[(4-fluorobenzyl)(methyl)amino]ethyl (Z)-2-acetyl-3-(1,3-benzodioxol-4-yl)-2-propenoate		C₂₂H₂₂FNO₅	详情	详情
(VIII)	13331	isopropyl (E)-3-amino-2-butenoate	143093-33-8	C₇H₁₃NO₂	详情	详情
(IX)	13332	isopropyl 3-oxobutanoate; Isopropyl acetoacetate	542-08-5	C₇H₁₂O₃	详情	详情
(X)	17615	2,3-Dimethoxybenzaldehyde	86-51-1	C₉H₁₀O₃	详情	详情
(XI)	12380	2,3-Dihydroxybenzaldehyde	24677-78-9	C₇H₆O₃	详情	详情

Extended Information