[(2S)-7-chloro-2,3-dihydro-1,4-benzodioxin-2-yl]methanol -Drug Synthesis Database

【结构式】

【分子编号】26411

【品名】[(2S)-7-chloro-2,3-dihydro-1,4-benzodioxin-2-yl]methanol

【CA登记号】

【分子式】C₉H₉ClO₃

【分子量】200.62136

【元素组成】C 53.88% H 4.52% Cl 17.67% O 23.92%

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：(V)

The reaction of 5-chloro-2-hydroxybenzaldehyde (I) with the chiral glycidyl tosylate (II) by means of K2CO3 in DMF gives the condensation product (III), which is oxidized with m-chloroperbenzoic acid to formyl ester (IV). The cyclization of (IV) with sodium methoxide in methanol affords the hydroxymethyl benzodioxane (V), which is tosylated with tosyl chloride in pyridine to the tosylate (VI). Finally, this compound is condensed with 1-(2-methoxyphenyl)piperidin-4-ylmethylamine (VII) by means of K2CO3 in refluxing acetonitrile.

参考文献中间体

合成目标

【1】 Birch, A.M.; Needham, P.L.; Kerrigan, F.; Gill, J.C.; Bradley, P.A.; N-substituted (2,3-dihydro-1,4-benzodioxin-2-yl)methylamine derivatives as D2 antagonists/5HT1A partial agonists with potential as atypical antipsychotic agents. J Med Chem 1999, 42, 17, 3342.

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)	26408	5-chlorosalicylaldehyde; 5-chloro-2-hydroxybenzaldehyde	635-93-8	C₇H₅ClO₂	详情	详情
(II)	16242	(2R)oxiranylmethyl 4-methylbenzenesulfonate; (2R)-(-)-Glycidyl tosylate	113826-06-5	C₁₀H₁₂O₄S	详情	详情
(III)	26409	5-chloro-2-[(2R)oxiranylmethoxy]benzaldehyde		C₁₀H₉ClO₃	详情	详情
(IV)	26410	5-chloro-2-[(2R)oxiranylmethoxy]phenyl formate		C₁₀H₉ClO₄	详情	详情
(V)	26411	[(2S)-7-chloro-2,3-dihydro-1,4-benzodioxin-2-yl]methanol		C₉H₉ClO₃	详情	详情
(VI)	26412	[(2R)-7-chloro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate		C₁₆H₁₅ClO₅S	详情	详情
(VII)	25196	[1-(2-methoxyphenyl)-4-piperidinyl]methylamine; [1-(2-methoxyphenyl)-4-piperidinyl]methanamine		C₁₃H₂₀N₂O	详情	详情

Extended Information