2-acetyl-6-[(3R,4R)-3-(acetoxy)-1-methylpiperidinyl]-3,5-dimethoxyphenyl 2-chlorobenzoate -Drug Synthesis Database

【结构式】

【分子编号】38043

【品名】2-acetyl-6-[(3R,4R)-3-(acetoxy)-1-methylpiperidinyl]-3,5-dimethoxyphenyl 2-chlorobenzoate

【CA登记号】

【分子式】C₂₅H₂₈ClNO₇

【分子量】489.95256

【元素组成】C 61.29% H 5.76% Cl 7.24% N 2.86% O 22.86%

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：(III)

The condensation of acetophenone (I) with 2-chlorobenzoyl chloride (II) in pyridine gives the corresponding ester (III), which is treated with KOH in hot pyridine yielding the diketone (IV). The cyclization of (IV) with H2SO4 in acetic acid at 100 C affords the benzopyranone (V). The hydrolysis of the acetate group of (V) with NaOH in methanol/water affords the piperidinol (VI), which is finally demethylated with pyridinium hydrochloride at 210-20 C. Alternatively, the ester (III) can be cyclized directly to benzopyranone (V) by means of NaH in hot dioxane.

参考文献中间体

合成目标

【1】 Naik, R.G.; Lal, B.; Rupp, R.H.; Sedlacek, H.H.; Dickneite, G.; Czech, J. (Aventis SA); Use of 4H-1-benzopyran-4-one derivs., 4H-1-benzopyran-4-one derivs. and medicines containing same. AU 8943841; DE 3836676; EP 0366061; JP 1990178225; US 5284856 .
【2】 Tabaka, A.C.; et al.; Application of modified flavone closure for the preparation of racemic L86-8275. Org Process Res Dev 1999, 3, 4, 256.

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)	38042	(3R,4R)-4-(3-acetyl-2-hydroxy-4,6-dimethoxyphenyl)-1-methylpiperidinyl acetate		C₁₈H₂₅NO₆	详情	详情
(II)	14000	o-Chlorobenzoyl chloride; 2-Chlorobenzoyl chloride	609-65-4	C₇H₄Cl₂O	详情	详情
(III)	38043	2-acetyl-6-[(3R,4R)-3-(acetoxy)-1-methylpiperidinyl]-3,5-dimethoxyphenyl 2-chlorobenzoate		C₂₅H₂₈ClNO₇	详情	详情
(IV)	38044	(3R,4R)-4-[3-[3-(2-chlorophenyl)-3-oxopropanoyl]-2-hydroxy-4,6-dimethoxyphenyl]-1-methylpiperidinyl acetate		C₂₅H₂₈ClNO₇	详情	详情
(V)	38045	(3R,4R)-4-[2-(2-chlorophenyl)-5,7-dimethoxy-4-oxo-4H-chromen-8-yl]-1-methylpiperidinyl acetate		C₂₅H₂₆ClNO₆	详情	详情
(VI)	38046	2-(2-chlorophenyl)-8-[(3R,4R)-3-hydroxy-1-methylpiperidinyl]-5,7-dimethoxy-4H-chromen-4-one		C₂₃H₂₄ClNO₅	详情	详情

Extended Information