1,4-dioxaspiro[4.5]dec-2-ylmethanamine; 1,4-dioxaspiro[4.5]dec-2-ylmethylamine -Drug Synthesis Database

【结构式】

【分子编号】62351

【品名】1,4-dioxaspiro[4.5]dec-2-ylmethanamine; 1,4-dioxaspiro[4.5]dec-2-ylmethylamine

【CA登记号】

【分子式】C₉H₁₇NO₂

【分子量】171.23952

【元素组成】C 63.13% H 10.01% N 8.18% O 18.69%

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：(IV)

The condensation of 2-(chloromethyl)-1,4-dioxaspiro[4,5]decane (I) with the sodium salt of phthalimide (II) in hot DMF affords the N-substituted phthalimide (III). Subsequent phthaloyl group hydrazinolysis gives the primary amine (IV). Finally, condensation of amine (IV) with S-methyl pseudothiourea sulfate (V) leads to the title guanidine derivative

参考文献中间体

合成目标

【1】 Aaron, J.E. Jr.; Hardie, W.R.; Process for the preparation of 1,3-dioxolan-4-yl-alcoyl-guanidines and its intermediates. FR 1522153 .

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)	62349	2-(chloromethyl)-1,4-dioxaspiro[4.5]decane		C₉H₁₅ClO₂	详情	详情
(II)	12376	Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione	85-41-6	C₈H₅NO₂	详情	详情
(III)	62350	2-(1,4-dioxaspiro[4.5]dec-2-ylmethyl)-1H-isoindole-1,3(2H)-dione		C₁₇H₁₉NO₄	详情	详情
(IV)	62351	1,4-dioxaspiro[4.5]dec-2-ylmethanamine; 1,4-dioxaspiro[4.5]dec-2-ylmethylamine		C₉H₁₇NO₂	详情	详情
(V)	10272	[[Amino(imino)methyl]sulfanyl]methane	2986-19-8	C₂H₆N₂S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

In a different method, acetylation of 3-amino-1,2-propanediol (I) yields the amide diol (II). Ketalization of cyclohexanone (III) with diol (II) furnishes the spiro dioxolane (IV). The acetamide function of (IV) is then hydrolyzed to amine (V) employing aqueous hydrazine. Amine (V) is condensed with N,N'-di-(carbobenzoxy)-N''-(trifluoromethylsulfonyl)guanidine (VI) to produce the protected guanidine (VII). The N-carbobenzoxy groups of (VII) are finally removed by hydrogenolysis over Pd/C. Alternatively, amine (V) is condensed with cyanogen bromide to produce the cyanamide (VIII). Then, reaction of cyanamide (VIII) with ammonium chloride in aqueous ammonia furnishes the title guanidine compound

参考文献中间体

合成目标

【1】 Xian, M.; Li, X.; Tang, X.; Chen, X.; Zheng, Z.; Galligan, J.J.; Kreulen, D.L.; Wang, P.G.; N-Hydroxyl derivatives of guanidine based drugs as enzymatic NO donors. Bioorg Med Chem Lett 2001, 11, 17, 2377.
【2】 Xiao, J.-H.; et al.; Endogenous retinoic acid receptor (RAR)-retinoid X receptor (RXR) heterodimers are the major functional forms regulating retinoid-responsive elements in adult human keratinocytes. Binding of ligands to RAR only is sufficient for RAR.RXR heterodimers to co. J Biol Chem 1995, 270, 7, 3001.

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)	12979	3-Amino-1,2-propanediol；3-aminopropane-1,2-diol	616-30-8	C₃H₉NO₂	详情	详情
(II)	62352	N-(2,3-dihydroxypropyl)acetamide		C₅H₁₁NO₃	详情	详情
(III)	11059	Cyclohexanone	108-94-1	C₆H₁₀O	详情	详情
(IV)	62353	N-(1,4-dioxaspiro[4.5]dec-2-ylmethyl)acetamide		C₁₁H₁₉NO₃	详情	详情
(V)	62351	1,4-dioxaspiro[4.5]dec-2-ylmethanamine; 1,4-dioxaspiro[4.5]dec-2-ylmethylamine		C₉H₁₇NO₂	详情	详情
(VI)	62354			C₁₈H₁₉N₃O₄	详情	详情
(VII)	62356	benzyl (Z)-{[(benzyloxy)carbonyl]amino}[(1,4-dioxaspiro[4.5]dec-2-ylmethyl)amino]methylidenecarbamate		C₂₆H₃₁N₃O₆	详情	详情
(VIII)	62355	1,4-dioxaspiro[4.5]dec-2-ylmethylcyanamide		C₁₀H₁₆N₂O₂	详情	详情

Extended Information