ethyl 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzoate -Drug Synthesis Database

【结构式】

【分子编号】50886

【品名】ethyl 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzoate

【CA登记号】

【分子式】C₁₆H₂₁NO₄

【分子量】291.34708

【元素组成】C 65.96% H 7.27% N 4.81% O 21.97%

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)

Condensation of ethyl 4-fluorobenzoate (I) with 4-piperidone ethylene ketal (II) afforded the N-arylpiperidine (III). Saponification of the ethyl ester group of (III), followed by acidic hydrolysis of the ethylene ketal function, yielded the benzoic acid derivative (V). Coupling of acid (V) with leucine ethyl ester (VI) using EDC gave amide (VII). Then, reductive amination of piperidone (VII) with the known arylethanolamine (VIII) using NaBH(OAc)3 furnished the aminopiperidine (IX). The ethyl ester group of (IX) was finally hydrolyzed with NaOH to provide the corresponding carboxylic acid.

参考文献中间体

合成目标

【1】 Hu, B.; et al.; (4-Piperidin-1-yl)phenyl amides: Potent and selective human beta3 agonists. J Med Chem 2001, 44, 9, 1456.
【2】 Taylor, E.C.; Skotnicki, J.S.; A convenient synthesis of 1-aryl-4-piperidones. Synthesis 1981, 606.

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)	22830	ethyl 4-fluorobenzoate	451-46-7	C₉H₉FO₂	详情	详情
(II)	11338	1,4-Dioxa-8-azaspiro[4.5]decane; 4-Piperidone ethylene ketal	177-11-7	C₇H₁₃NO₂	详情	详情
(III)	50886	ethyl 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzoate		C₁₆H₂₁NO₄	详情	详情
(IV)	50887	4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzoic acid		C₁₄H₁₇NO₄	详情	详情
(V)	50888	4-(4-oxo-1-piperidinyl)benzoic acid		C₁₂H₁₃NO₃	详情	详情
(VI)	50889	ethyl (2S)-2-amino-4-methylpentanoate		C₈H₁₇NO₂	详情	详情
(VII)	50890	ethyl (2S)-4-methyl-2-[[4-(4-oxo-1-piperidinyl)benzoyl]amino]pentanoate		C₂₀H₂₈N₂O₄	详情	详情
(VIII)	49404	N-[5-[(1R)-2-amino-1-hydroxyethyl]-2-hydroxyphenyl]methanesulfonamide		C₉H₁₄N₂O₄S	详情	详情
(IX)	50891	ethyl (2S)-2-[(4-[4-[((2R)-2-hydroxy-2-[4-hydroxy-3-[(methylsulfonyl)amino]phenyl]ethyl)amino]-1-piperidinyl]benzoyl)amino]-4-methylpentanoate		C₂₉H₄₂N₄O₇S	详情	详情

Extended Information