(1R)-2-[benzyl[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amino]-1-[4-(benzyloxy)-3-nitrophenyl]-1-ethanol -Drug Synthesis Database

【结构式】

【分子编号】33901

【品名】(1R)-2-[benzyl[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amino]-1-[4-(benzyloxy)-3-nitrophenyl]-1-ethanol

【CA登记号】

【分子式】C₃₂H₃₄N₂O₅

【分子量】526.63244

【元素组成】C 72.98% H 6.51% N 5.32% O 15.19%

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 bromination of 4 benzyloxy-3-nitroacetophenone (I) with Br2 in CHCl3 gives 4-benzyloxy-3-nitro-alpha-bromoacetophenone (II), which is then condensed with N-benzyl-N-(1-methyl-2-(p-methoxyphenyl)ethyl]-amine (III) in butanone at 80 C yielding 4-benzyloxy-3-nitro-alpha-[N-benzyl-N-[1-methyl-2-(p-methoxyphenyl)ethyl]amino]acetophenone (IV). The reduction of the carbonyl group of (IV) with NaBH4 in ethanol affords the corresponding nitro alcohol (V), which is reduced again with Fe and HCl in ethanol - water to the amino alcohol (VI). The formylation of (VI) with formic acid in acetic anhydride gives 4-benzyloxy-3-formyl-amino-alpha-[N-benzyl-N-[1-methyl-2-(p-methoxyphenyl)ethyl]aminomethyl]benzyl alcohol (VII), which is finally debenzylated with H2 over Pd/C in ethanol and treated with fumaric acid (A).

参考文献中间体

合成目标

【1】 Murakami, M.; et al.; alpha-Aminomethylbenzylalkoholderivative. DE 2305092; DE 2366625 .
【2】 Castaner, J.; Weetman, D.F.; BD 40A. Drugs Fut 1977, 2, 10, 639.

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)	23808	Fumaric acid; (E)-2-butenedioic acid	110-17-8	C₄H₄O₄	详情	详情
(I)	20627	1-[4-(benzyloxy)-3-nitrophenyl]-1-ethanone		C₁₅H₁₃NO₄	详情	详情
(II)	32763	1-[4-(benzyloxy)-3-nitrophenyl]-2-bromo-1-ethanone		C₁₅H₁₂BrNO₄	详情	详情
(III)	33904	(2S)-N-benzyl-1-(4-methoxyphenyl)-2-propanamine; N-benzyl-N-[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amine		C₁₇H₂₁NO	详情	详情
(IV)	33900	2-[benzyl[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amino]-1-[4-(benzyloxy)-3-nitrophenyl]-1-ethanone		C₃₂H₃₂N₂O₅	详情	详情
(V)	33901	(1R)-2-[benzyl[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amino]-1-[4-(benzyloxy)-3-nitrophenyl]-1-ethanol		C₃₂H₃₄N₂O₅	详情	详情
(VI)	33902	(1R)-1-[3-amino-4-(benzyloxy)phenyl]-2-[benzyl[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amino]-1-ethanol		C₃₂H₃₆N₂O₃	详情	详情
(VII)	33903	5-((1R)-2-[benzyl[(1S)-2-(4-methoxyphenyl)-1-methylethyl]amino]-1-hydroxyethyl)-2-(benzyloxy)phenylformamide		C₃₃H₃₆N₂O₄	详情	详情

Extended Information