2-(bromomethyl)oxirane -Drug Synthesis Database

【结构式】

【分子编号】29679

【品名】2-(bromomethyl)oxirane

【CA登记号】3132-64-7

【分子式】C₃H₅BrO

【分子量】136.9761

【元素组成】C 26.31% H 3.68% Br 58.33% O 11.68%

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：(B)

This 1-vinylimidazole compound (II) is obtained by reaction of N,N'-thionyldiimidazole (A) with 2-hydroxy-3,6-dichloroacetophenone (I) in dichloro-methane. Treatment of (II) with epibromohydrin (B) in DMF in the presence of NaH gives the epoxy compound (III), which is then treated with isopropylamine (C) to obtain the propanolamine compound (IV). The hydrochloride can be prepared by treatment of the free base (IV) with one molar equivalent of HCl in AcOEt.

参考文献中间体

合成目标

【1】 Kida, S.; Ueda, M.; Kimoto, S.; Haruna, M.; Matsumoto, H.; Takahashi, K.; Ogata, M.; Synthesis and antiarrhythmic activity of new 1-[1-[2-[3-(alkylamino)-2-hydroxypropoxy]phenyl]vinyl]-1H-imidazoles and related compounds. J Med Chem 1984, 27, 9, 1142.
【2】 Ueda, M.; 711389-S. Drugs Fut 1985, 10, 6, 472.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	29655	1-(1H-imidazol-1-ylsulfinyl)-1H-imidazole		C₆H₆N₄OS	详情	详情
(B)	29679	2-(bromomethyl)oxirane	3132-64-7	C₃H₅BrO	详情	详情
(I)	29677	1-(3,6-dichloro-2-hydroxyphenyl)-1-ethanone		C₈H₆Cl₂O₂	详情	详情
(II)	29678	3,6-dichloro-2-[1-(1H-imidazol-1-yl)vinyl]phenol		C₁₁H₈Cl₂N₂O	详情	详情
(III)	29680	3,6-dichloro-2-[1-(1H-imidazol-1-yl)vinyl]phenyl 2-oxiranylmethyl ether; 1-[1-[3,6-dichloro-2-(2-oxiranylmethoxy)phenyl]vinyl]-1H-imidazole		C₁₄H₁₂Cl₂N₂O₂	详情	详情
(IV)	29681	1-[3,6-dichloro-2-[1-(1H-imidazol-1-yl)vinyl]phenoxy]-3-(isopropylamino)-2-propanol		C₁₇H₂₁Cl₂N₃O₂	详情	详情
(C)	23933	2-Propanamine; Isopropylamine	75-31-0	C₃H₉N	详情	详情

合成路线2

该中间体在本合成路线中的序号：(A)

This compound can be obtained in two different ways: 1) The reaction of cyclopropylmethyl ketone oxime (II) with epibromohydrin (A) in THF containing NaH gives O-[2,3-epoxypropyl]cyclopropylmethyl ketone oxime (III), which is treated with excess tert-butylamine (C) in ethanol yielding the final compound. 2) By condensation of cyclopropylmethyl ketone (I) with 3-(aminooxy)-N-tert-butyl-2-hydroxypropanamine (B) in ethanol.

参考文献中间体

合成目标

【1】 Leclerc, G.; Bouzoubaa, M.; Andermann, G.; Ethers and oxime ethers of alkylamino alcohols as medicaments and novel products, and processes for their preparation. AU 1167283; EP 0087378; FR 2521856; JP 58154538; US 4766151 .
【2】 Schwartz, J.; Bieth, N.; Leclerc, G.; Synthesis and beta-adrenergic blocking activity of a new aliphatic oxime ethers. J Med Chem 1980, 23, 6, 620.
【3】 Castaner, J.; Serradell, M.N.; Falintolol oxalate. Drugs Fut 1984, 9, 7, 510.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	29679	2-(bromomethyl)oxirane	3132-64-7	C₃H₅BrO	详情	详情
(B)	34255	1-(aminooxy)-3-(tert-butylamino)-2-propanol		C₇H₁₈N₂O₂	详情	详情
(I)	12435	Acetylcyclopropane; 1-Cyclopropyl-1-ethanone; Cyclopropylmethylketone	765-43-5	C₅H₈O	详情	详情
(II)	34253	1-cyclopropyl-1-ethanone oxime		C₅H₉NO	详情	详情
(III)	34254	1-cyclopropyl-1-ethanone O-(2-oxiranylmethyl)oxime		C₈H₁₃NO₂	详情	详情
(C)	17895	2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine	75-64-9	C₄H₁₁N	详情	详情

合成路线3

该中间体在本合成路线中的序号：(VIII)

Alkylation of 5-hydroxyisoquinoline (VII) with epibromohydrin (VIII) produced the glycidyl ether (IX). Subsequent epoxide ring opening in (IX) with aniline (VI) furnished the target (isoquinolyloxy)propanolamine.

参考文献中间体

合成目标

【1】 Aubriot, S.; et al.; New series of aryloxypropanolamines with both human beta3-adrenoceptor agonistic activity and free radical scavenging properties. Bioorg Med Chem Lett 2002, 12, 2, 209.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	59679	4-[3-(4-aminophenoxy)propyl]-2,6-di(tert-butyl)phenol		C₂₃H₃₃NO₂	详情	详情
(VII)	18668	5-isoquinolinol	2439-04-5	C₉H₇NO	详情	详情
(VIII)	29679	2-(bromomethyl)oxirane	3132-64-7	C₃H₅BrO	详情	详情
(IX)	59680	5-isoquinolinyl 2-oxiranylmethyl ether; 5-(2-oxiranylmethoxy)isoquinoline		C₁₂H₁₁NO₂	详情	详情

Extended Information