Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine -Drug Synthesis Database

【结构式】

【分子编号】27335

【品名】Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine

【CA登记号】4795-29-3

【分子式】C₅H₁₁NO

【分子量】101.14848

【元素组成】C 59.37% H 10.96% N 13.85% O 15.82%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(IV)

2-Methoxy-5-(N-methylmethanesulfonamido)-N-tetrahydrofurfurylbenzamide (II), which is prepared from (I) and tetrahydrofurfurylamine, is treated with SOCl2 in dichloroethane to give the dichloro compound (III). Treatment of (III) with EtNH2 gives title compound.

参考文献中间体

合成目标

【1】 Masaru, O.; Hiroshi, M. (Shionogi & Co. Ltd.); Meta-sulfonamido-benzamides. DE 2803651; ES 466366; FR 2378758; GB 1557019; US 4328155; US 4328344; US 4330472; US 4350635; US 4351770; US 44313663 .
【2】 Ogata, M.; 710723-S. Drugs Fut 1985, 10, 9, 758.

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)	27331	2-methoxy-5-[methyl(methylsulfonyl)amino]benzoic acid		C₁₀H₁₃NO₅S	详情	详情
(II)	27333	2-methoxy-5-[methyl(methylsulfonyl)amino]-N-(tetrahydro-3-furanylmethyl)benzamide		C₁₅H₂₂N₂O₅S	详情	详情
(III)	27334	N-(2,5-dichloropentyl)-2-methoxy-5-[methyl(methylsulfonyl)amino]benzamide		C₁₅H₂₂Cl₂N₂O₄S	详情	详情
(IV)	27335	Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine	4795-29-3	C₅H₁₁NO	详情	详情
(V)	10928	Ethanamine	75-04-7	C₂H₇N	详情	详情

合成路线2

该中间体在本合成路线中的序号：(LXVII)

Tetrahydrofurfurylamine (XLVII) was converted into the corresponding phthalimide (XLVIII) by reaction of phthalic anhydride (V) in boiling chloroform. Subsequent ruthenium-catalyzed oxidation of (XLVIII) produced keto acid (XI), along with a pentanolide by-product, which was removed by column chromatography. Finally, acid hydrolysis of (XI) led to the desired compound. A closely related strategy was based in the ruthenium oxidation of N-benzoyl tetrahydrofurfurylamine (LXX), prepared from amine (XLVII) and benzoyl chloride (XLIX), to afford 5-benzoylaminolevulinic acid (XXXV), which was then hydrolyzed in boiling 6 N HCl .

参考文献中间体

合成目标

【1】 Kawakami, H.; et al.; A new synthesis of 5-aminolevulinic acid. Agric Biol Chem 1991, 55, 6, 1687.
【2】 Matsumoto, K.; Kawakami, H.; Koseki, K.; Ebata, T.; Matsushita, H. (Japan Tobacco Inc.); Method of preparing an acid additional salt of delta-aminolevulinic acid. US 5284973 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	11900	2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride	85-44-9	C₈H₄O₃	详情	详情
(XI)	59147	5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoic acid		C₁₃H₁₁NO₅	详情	详情
(XXXV)	59156	5-(benzoylamino)-4-oxopentanoic acid		C₁₂H₁₃NO₄	详情	详情
(LXVII)	27335	Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine	4795-29-3	C₅H₁₁NO	详情	详情
(LXVIII)	59191	2-(tetrahydro-2-furanylmethyl)-1H-isoindole-1,3(2H)-dione		C₁₃H₁₃NO₃	详情	详情
(LXIX)	10463	Benzoyl chloride	98-88-4	C₇H₅ClO	详情	详情
(LXX)	59192	N-(tetrahydro-2-furanylmethyl)benzamide		C₁₂H₁₅NO₂	详情	详情

合成路线3

该中间体在本合成路线中的序号：(VI)

The reaction of m-xylene-alpha,alpha'-diamine (I) with N,N'-bis(tert-butoxycarbonyl)pyrazole-1-carboxamidine (II) in THF gives the protected guanidine (III), which is acylated at the free amino group with 2,3-diphenylpropionyl chloride (IV) and triethylamine in dichloromethane affording the amide (V). The condensation of (V) with tetrahydrofuran-2-ylmethylamine (VI) in refluxing THF affords the protected amidinourea (VII), which is finally treated with TFA in dichloromethane.

参考文献中间体

合成目标

【1】 Biftu, T.; et al.; Synthesis and SAR of oxodiazole benzenesulfonamides as selective beta3 adrenergic receptor agonist antiobesity agents. 217th ACS Natl Meet (March 21 1999, Anaheim) 1999, Abst MEDI 138.

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)	19167	3-(aminomethyl)benzylamine; [3-(aminomethyl)phenyl]methanamine	1477-55-0	C₈H₁₂N₂	详情	详情
(II)	29482	N,N-bis-Boc-1-guanylpyrazole; tert-butyl (E)-[(tert-butoxycarbonyl)amino](1H-pyrazol-1-yl)methylidenecarbamate	152120-54-2	C₁₄H₂₂N₄O₄	详情	详情
(III)	29483	tert-butyl (Z)-[[3-(aminomethyl)benzyl]amino][(tert-butoxycarbonyl)amino]methylidenecarbamate		C₁₉H₃₀N₄O₄	详情	详情
(IV)	29484	2,3-diphenylpropanoyl chloride		C₁₅H₁₃ClO	详情	详情
(V)	29485	tert-butyl (Z)-[(tert-butoxycarbonyl)amino][(3-[[(2,3-diphenylpropanoyl)amino]methyl]benzyl)amino]methylidenecarbamate		C₃₄H₄₂N₄O₅	详情	详情
(VI)	27335	Tetrahydro-2-furanylmethanamine; Tetrahydrofurfurylamine	4795-29-3	C₅H₁₁NO	详情	详情
(VII)	29486	tert-butyl (Z)-[(3-[[(2,3-diphenylpropanoyl)amino]methyl]benzyl)amino]([[(tetrahydro-2-furanylmethyl)amino]carbonyl]amino)methylidenecarbamate		C₃₅H₄₃N₅O₅	详情	详情

Extended Information