4-(4-pyridinyl)-1-butanol -Drug Synthesis Database

【结构式】

【分子编号】59550

【品名】4-(4-pyridinyl)-1-butanol

【CA登记号】

【分子式】C₉H₁₃NO

【分子量】151.20836

【元素组成】C 71.49% H 8.67% N 9.26% O 10.58%

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：(XX)

In a different strategy, the lithium derivative of 4-picoline (XVII) was alkylated with 2-(3-bromopropoxy)tetrahydropyran (XVIII) to afford (XIX). Acidic hydrolysis of the tetrahydropyranyl protecting group furnished 4-(4-pyridinyl)butanol (XX). Alternatively, lithiation of 4-picoline (XVII), followed by alkylation with 1-bromo-3-chloropropane (XXI) gave rise to 4-(4-pyridinyl)butyl chloride (XXII).

参考文献中间体

合成目标

【1】 Chung, J.Y.L.; Zhao, D.; Hughes, D.L. (Merck & Co., Inc.); Process for preparing fibrinogen receptor antagonists. US 5312923; WO 9316994 .
【2】 Chung, J.Y.L.; Zhao, D.; Hughes, D.L. (Merck & Co., Inc.); Process for preparing fibrinogen receptor antagonists. WO 9316995 .
【3】 Chung, J.Y.L.; Zhao, D.; Hughes, D.L.; Grabowski, E.E.; A practical synthesis of fibrinogen receptor antagonist MK-383 - Selective functionalization of (S)-tyrosine. Tetrahedron 1993, 49, 26, 5767.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XVII)	31150	4-methylpyridine	108-89-4	C₆H₇N	详情	详情
(XVIII)	42252	3-bromopropyl tetrahydro-2H-pyran-2-yl ether; 2-(3-bromopropoxy)tetrahydro-2H-pyran		C₈H₁₅BrO₂	详情	详情
(XIX)	59549	4-(4-pyridinyl)butyl tetrahydro-2H-pyran-2-yl ether; 4-[4-(tetrahydro-2H-pyran-2-yloxy)butyl]pyridine		C₁₄H₂₁NO₂	详情	详情
(XX)	59550	4-(4-pyridinyl)-1-butanol		C₉H₁₃NO	详情	详情
(XXI)	10358	1-Bromo-3-chloropropane	109-70-6	C₃H₆BrCl	详情	详情
(XXII)	59551	4-(4-chlorobutyl)pyridine		C₉H₁₂ClN	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XX)

Tyrosine methyl ester (XXIII) was acylated with butanesulfonyl chloride (XIV) in the presence of pyridine to produce sulfonamide (XXIV). Mitsunobu coupling of pyridinyl butanol (XX) with the phenolic compound (XXIV) furnished ether (XXV). Subsequent hydrolysis of the methyl ester group of (XXV) employing LiOH afforded acid (XXVI). The title piperidine compound was then obtained by catalytic hydrogenation of the pyridine ring of (XXVI) in the presence of Pd/C.

参考文献中间体

合成目标

【1】 Chung, J.Y.L.; Zhao, D.; Hughes, D.L. (Merck & Co., Inc.); Process for preparing fibrinogen receptor antagonists. US 5312923; WO 9316994 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIV)	26779	1-butanesulfonyl chloride	2386-60-9	C₄H₉ClO₂S	详情	详情
(XX)	59550	4-(4-pyridinyl)-1-butanol		C₉H₁₃NO	详情	详情
(XXIII)	21431	methyl (2S)-2-amino-3-(4-hydroxyphenyl)propanoate	1080-06-4	C₁₀H₁₃NO₃	详情	详情
(XXIV)	59552	methyl (2S)-2-[(butylsulfonyl)amino]-3-(4-hydroxyphenyl)propanoate		C₁₄H₂₁NO₅S	详情	详情
(XXV)	59553	methyl (2S)-2-[(butylsulfonyl)amino]-3-{4-[4-(4-pyridinyl)butoxy]phenyl}propanoate		C₂₃H₃₂N₂O₅S	详情	详情
(XXVI)	59554	(2S)-2-[(butylsulfonyl)amino]-3-{4-[4-(4-pyridinyl)butoxy]phenyl}propanoic acid		C₂₂H₃₀N₂O₅S	详情	详情

Extended Information