(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyltetrahydro-1(2H)-pyridiniumyl]propanoate -Drug Synthesis Database

【结构式】

【分子编号】67023

【品名】(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyltetrahydro-1(2H)-pyridiniumyl]propanoate

【CA登记号】　

【分子式】C₂₃H₂₉NO₃

【分子量】367.4882

【元素组成】C 75.17% H 7.95% N 3.81% O 13.06%

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：(XI)

参考文献中间体

合成目标

【1】 Buehler JD. 2007. Process for preparing alvimopan and their compositions containing opioid antagonists. WO 2007047935(Adolor Corp., USA).
【2】 Copley-Merriman CR, Maki J, Barnett CJ. 1989. Synthesis of picenadol via metalloenamine alkylation methodology. J Org Chem, 54(4): 795～800.
【3】 Frank SA, Prather DE, Ward JA, et al. 1995. Preparation of 3,4,4-trisubtituted piperidinyl N-alkylcarboxylates and intermediates, useful as opioid antagonists. EP 657428(Eli Lilly and Co., USA)
【4】 Robey RL, Evans DA, Zimmerman DM, et al. 1980. Application of metalated enamines to alkaloid synthesis. An expedient approach to the synthesis of morphine-based analgesics. J Am Chem Soc, 102(5): 955～956
【5】 Werner JA, Cerbone LR, Frank SA, et al. 1996. Synthesis of trans-3,4-dimethyl-(3-hydroxyphenyl)piperidine opioid antagonists: application of the cis-thermal elimination of carbonates to alkaloid synthesis. J Org Chem, 61(2):587～597

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	16621	(3R,4R)-1-[(2S)-2-benzyl-3-methoxy-3-oxopropyl]-4-(3-hydroxyphenyl)-3,4-dimethylhexahydropyridinium chloride		C₂₄H₃₂ClNO₃	详情	详情
(I)	16614	1,3-dimethyltetrahydro-4(1H)-pyridinone; 1,3-Dimethyl-4-piperidone	4629-80-5	C₇H₁₃NO	详情	详情
(II)	66993	(3-isopropoxyphenyl)lithium		C₉H₁₁LiO	详情	详情
(III)	16615	(3S,4R)-4-(3-isopropoxyphenyl)-1,3-dimethylhexahydro-4-pyridinol		C₁₆H₂₅NO₂	详情	详情
(IV)	16616	ethyl (3S,4R)-4-(3-isopropoxyphenyl)-1,3-dimethylhexahydro-4-pyridinyl carbonate		C₁₉H₂₉NO₄	详情	详情
(V)	16617	(3R)-4-(3-isopropoxyphenyl)-1,3-dimethyl-1,2,3,6-tetrahydropyridine; 3-[(3R)-1,3-dimethyl-1,2,3,6-tetrahydro-4-pyridinyl]phenyl isopropyl ether		C₁₆H₂₃NO	详情	详情
(VI)	67021			C₁₇H₂₅NO	详情	详情
(VII)	16618	(3R,4R)-4-(3-isopropoxyphenyl)-1,3,4-trimethylhexahydropyridine; isopropyl 3-[(3R,4R)-1,3,4-trimethylhexahydro-4-pyridinyl]phenyl ether		C₁₇H₂₇NO	详情	详情
(VIII)	16620	3-[(3R,4R)-3,4-dimethylhexahydro-4-pyridinyl]phenol	119193-19-0	C₁₃H₁₉NO	详情	详情
(IX)	67022	methyl 3-((3S,4S)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)propanoate		C₁₇H₂₅NO₃	详情	详情
(XI)	67023	(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyltetrahydro-1(2H)-pyridiniumyl]propanoate		C₂₃H₂₉NO₃	详情	详情
(XII)	67024	tert-butyl 2-(2-benzyl-3-(4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)propanamido)acetate		C₂₉H₄₀N₂O₄	详情	详情
(XIII)	67025	2-([(2S)-2-([(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)propanamido)acetic acid		C₂₅H₃₂N₂O₄	详情	详情

Extended Information