1-[4-(Benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)amino]-1-ethanone; N-(3,4-Dimethoxyphenylethyl)-4-benzyloxyphenacylamine -Drug Synthesis Database

【结构式】

【分子编号】10100

【品名】1-[4-(Benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)amino]-1-ethanone; N-(3,4-Dimethoxyphenylethyl)-4-benzyloxyphenacylamine

【CA登记号】

【分子式】C₂₅H₂₇NO₄

【分子量】405.49372

【元素组成】C 74.05% H 6.71% N 3.45% O 15.78%

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：(I)

A new enantioselective synthesis for denopamine has been reported: The acylation of 1-(4-benzyloxyphenyl)-2-[2-(3,4-dimethoxyphenyl)ethylamino]ethanone (I) with benzyloxycarbonyl chloride (II) by means of NaHCO3 in dichloromethane gives the protected aminoketone (III), which is submitted to an asymmetric reduction with (R)-(+)-2-amino-3-methyl-1,1-diphenyl-1-butanol-borane complex in THF yielding the (R)-(-)-protected alcohol (V). Finally, the debenzylation of (V) by hydrogenolysis with H2 over Pd/C in methanol affords denopamine with 96% optical purity.

参考文献中间体

合成目标

【1】 Takeda, M.; Saito, K.; Kawaguchi, T.; Matsuki, K.; Iwakuma, T.; Asymmetric reduction of aromatic ketones. I. Enantioselective synthesis of denopamine. Chem Pharm Bull 1993, 41, 4, 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
(I)	10100	1-[4-(Benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)amino]-1-ethanone; N-(3,4-Dimethoxyphenylethyl)-4-benzyloxyphenacylamine		C₂₅H₂₇NO₄	详情	详情
(II)	10101	Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene	501-53-1	C₈H₇ClO₂	详情	详情
(III)	10102	Benzyl 2-[4-(benzyloxy)phenyl]-2-oxoethyl(3,4-dimethoxyphenethyl)carbamate; Benzyl (4-benzyloxy)phenacyl-(3,4-dimethoxyphenethyl)carbamate		C₃₃H₃₃NO₆	详情	详情
(IV)	10103	(2R)-2-Amino-3-methyl-1,1-diphenyl-1-butanol	56755-20-5 (hydrochloride)	C₁₇H₂₁NO	详情	详情
(V)	10104	benzyl (2R)-2-[4-(benzyloxy)phenyl]-2-hydroxyethyl(3,4-dimethoxyphenethyl)carbamate		C₃₃H₃₅NO₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(XVI)

The condensation of 4-benzyloxyphenacyl chloride (XV) with the amine (IV) in refluxing CH2Cl2 gives N-(3,4-dimethoxyphenylethyl)-4-benzyloxyphenacylamine (XVI), which is reduced with NaSH4 in ethanol, also affording the protected product (VI).

参考文献中间体

合成目标

【1】 Ikezaki, M.; Ito, N.; Okazaki, Y.; Hoshiyama, M.; Nagao, T. (Tanabe Seiyaku Co., Ltd.); Benzyl alcohol, amine derivatives. AT 343628B; BE 0833731; DE 2542881; FR 2326182; GB 1499345; JP 50157327; JP 53010974; JP 7795620; JP 7795621; NL 7511564; US 4032575; US 4072759 .
【2】 Blancafort, P.; Castaner, J.; Serradell, M.N.; TA-064. Drugs Fut 1982, 7, 6, 407.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	10098	2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine	120-20-7	C₁₀H₁₅NO₂	详情	详情
(VI)	31687	(1R)-1-[4-(benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)amino]-1-ethanol		C₂₅H₂₉NO₄	详情	详情
(XV)	31689	4-Benzyloxyphenacyl chloride; 1-[4-(Benzyloxy)phenyl]-2-chloro-1-ethanone	39188-62-0	C₁₅H₁₃ClO₂	详情	详情
(XVI)	10100	1-[4-(Benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)amino]-1-ethanone; N-(3,4-Dimethoxyphenylethyl)-4-benzyloxyphenacylamine		C₂₅H₂₇NO₄	详情	详情

Extended Information