2-(3-bromo-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione -Drug Synthesis Database

【结构式】

【分子编号】59158

【品名】2-(3-bromo-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione

【CA登记号】

【分子式】C₁₁H₁₀BrNO₃

【分子量】284.10934

【元素组成】C 46.5% H 3.55% Br 28.12% N 4.93% O 16.89%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XXX)

Alkylation of potassium phthalimide (XXVII) with epichlorohydrin (XXVIII) provided N-glycidyl phthalimide (XXIX). Epoxide ring opening in (XXIX) with aqueous HBr led to bromohydrin (XXX), which was further oxidized to bromo ketone (XXXI) by means of CrO3. Coupling of bromo ketone (XXXI) with diethyl malonate (XXXII) to afford (XXXIII) was accomplished in the presence of NaOEt in EtOH/DMF as the solvent. Acid hydrolysis of the malonate ester (XXXIII), followed by thermal decarboxylation, gave rise to phthalimido levulinic acid (XI). The phthaloyl group of (XI) was finally hydrolyzed under acidic conditions to furnish delta-aminolevulinic acid.

参考文献中间体

合成目标

【1】 Collins, A.; Tschudy, D.P.; Malonic ester synthesis of delta-aminolevulinic acid. The reaction of N-3-bromoacetonylphthalimide with malonic ester. J Org Chem 1959, 24, 556.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XI)	59147	5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoic acid		C₁₃H₁₁NO₅	详情	详情
(XXVII)	27890	Potassium phthalimide	1074-82-4	C₈H₄KNO₂	详情	详情
(XXVIII)	10246	N-Phenyl-2-[(triphenylstannyl)selanyl]benzamide		C₃₁H₂₅NOSeSn	详情	详情
(XXIX)	12335	2-(2-Oxiranylmethyl)-1H-isoindole-1,3(2H)-dione; N-(2,3-Epoxypropyl)phtalimide	5455-98-1	C₁₁H₉NO₃	详情	详情
(XXX)	59158	2-(3-bromo-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione		C₁₁H₁₀BrNO₃	详情	详情
(XXXI)	59159	2-(3-Bromo-2-oxopropyl)isoindole-1,3-dione		C₁₁H₈BrNO₃	详情	详情
(XXXII)	16829	Diethyl malonate	105-53-3	C₇H₁₂O₄	详情	详情
(XXXIII)	59160	diethyl 2-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-oxopropyl]malonate		C₁₈H₁₉NO₇	详情	详情

Extended Information