methyl (1R,2S)-1-hydroxy-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】46774

【品名】methyl (1R,2S)-1-hydroxy-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylate

【CA登记号】

【分子式】C₁₃H₁₆O₄

【分子量】236.26764

【元素组成】C 66.09% H 6.83% O 27.09%

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：(I)

Dehydroxylation of compound (I) by hydrogenation over Pd/C in MeOH provides tetralinecarboxylic acid methyl ester (II), which is then reduced by means of LiAlH4 in THF to afford tetralinemethanol as a mixture of enantiomers (III). Separation of isomers in (III) is then achieved by first acylation of the alcohol with (-)-menthyl chloroformate (IV) in pyridine, followed by the separation of the two resulting diastereomers by recrystallization to give (-)-menthyl carbonate (V) and its subsequent hydrolysis with NaOH in THF/H2O to furnish compound (VI).

参考文献中间体

合成目标

【1】 Tsubaki, K.; Hattori, K.; Tabuchi, S.; Okitsu, O.; Sakane, K.; Tanaka, H.; Taniguchi, K.; A novel pyridazinone derivative as a nonprostanoid PGI2 agonist. Bioorg Med Chem Lett 2000, 10, 24, 2787.
【2】 Taniguchi, K.; Nagano, M.; Hattori, K.; Tsubaki, K.; Okitsu, O.; Tabuchi, S. (Fujisawa Pharmaceutical Co., Ltd.); Naphthalene derivs. as prostaglandin I2 agonists. EP 0749424; JP 1997509958; US 5763489; WO 9524393 .

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)	46774	methyl (1R,2S)-1-hydroxy-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylate		C₁₃H₁₆O₄	详情	详情
(II)	46775	methyl (2S)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylate		C₁₃H₁₆O₃	详情	详情
(III)	46776	(5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl)methanol		C₁₂H₁₆O₂	详情	详情
(IV)	46777	(1S,2R,4R)-2-[(chlorocarbonyl)oxy]-1-isopropyl-4-methylcyclohexane	14602-86-9	C₁₁H₁₉ClO₂	详情	详情
(V)	46778	(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl [(2S)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]methyl carbonate		C₂₃H₃₄O₄	详情	详情
(VI)	46779	[(2S)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]methanol		C₁₂H₁₆O₂	详情	详情
(VII)	46780	1,1-diphenylacetone	781-35-1	C₁₅H₁₄O	详情	详情
(VIII)	15618	2-Oxoacetic acid; Glyoxylic Acid	298-12-4	C₂H₂O₃	详情	详情
(IX)	46781	2-hydroxy-4-oxo-5,5-diphenylpentanoic acid		C₁₇H₁₆O₄	详情	详情
(X)	46782	6-benzhydryl-1,6-dihydro-3(2H)-pyridazinone		C₁₇H₁₆N₂O	详情	详情
(XI)	46783	6-benzhydryl-2-[[(2S)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]methyl]-1,6-dihydro-3(2H)-pyridazinone		C₂₉H₃₀N₂O₂	详情	详情
(XII)	46784	6-benzhydryl-2-[[(2S)-5-hydroxy-1,2,3,4-tetrahydro-2-naphthalenyl]methyl]-1,6-dihydro-3(2H)-pyridazinone		C₂₈H₂₈N₂O₂	详情	详情
(XIII)	16640	Ethyl 2-bromoacetate; Ethyl bromoacetate	105-36-2	C₄H₇BrO₂	详情	详情
(XIV)	46785	ethyl 2-[((6S)-6-[[3-benzhydryl-6-oxo-3,6-dihydro-1(2H)-pyridazinyl]methyl]-5,6,7,8-tetrahydro-1-naphthalenyl)oxy]acetate		C₃₂H₃₄N₂O₄	详情	详情

Extended Information