2-[4-(benzyloxy)phenyl]-2-oxoacetaldehyde; 4-benzyloxy-alpha-oxophenylacetaldehyde -Drug Synthesis Database

【结构式】

【分子编号】31696

【品名】2-[4-(benzyloxy)phenyl]-2-oxoacetaldehyde; 4-benzyloxy-alpha-oxophenylacetaldehyde

【CA登记号】

【分子式】C₁₅H₁₂O₃

【分子量】240.25848

【元素组成】C 74.99% H 5.03% O 19.98%

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：(XVII)

The oxidation of 4-benzyloxyphenacyl chloride (XV) with KI and DMSO gives 4-benzyloxy-alpha-oxophenylacetaldehyde (XVII), which is condensed with the amine (IV) to afford the corresponding Schiff base (XVIII). Finally, this compound is reduced with NaBH4 yielding the protected product (VI), already obtained.

参考文献中间体

合成目标

【1】 Ikezaki, M.; Umino, N.; Iwakuma, T.; Process for preparation of benzyl alcohol derivatives. JP 52051334 .
【2】 Ikezaki, M.; Umino, N.; Iwakuma, T.; Process for preparation of benzyl alcohol derivatives. JP 52051335 .
【3】 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
(XVII)	31696	2-[4-(benzyloxy)phenyl]-2-oxoacetaldehyde; 4-benzyloxy-alpha-oxophenylacetaldehyde		C₁₅H₁₂O₃	详情	详情
(XVIII)	31697	1-[4-(benzyloxy)phenyl]-2-[(3,4-dimethoxyphenethyl)imino]-1-ethanone		C₂₅H₂₅NO₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The oxidation of (VI) with SeO2 in hot dioxane-water gives 4-benzyloxyphenylglyoxal (IV). The condensation with (II) in refluxing ethanol, gives 4-benzyloxy-alpha-[1,1-dimethyl-3-(2-methoxyphenyl)propylimino]acetophenone (V), which is then reduced with NaBH4 in ethanol to afford (III), which is debenzylated by reduction with H2 over Pd/C in ethanol, and treated with HCl.

参考文献中间体

合成目标

【1】 Olsson, O.A.T.; Persson, N.H.A.; Svensson, L.A.; Waldeck, C.B.; Wetterlin, K.J.L.; EP 0004835 .
【2】 Castaner, J.; Blancafort, P.; Serradell, M.N.; D-2343. Drugs Fut 1982, 7, 1, 17.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	36422	3-(2-methoxyphenyl)-1,1-dimethylpropylamine; 4-(2-methoxyphenyl)-2-methyl-2-butanamine		C₁₂H₁₉NO	详情	详情
(III)	36426	1-[4-(benzyloxy)phenyl]-2-[[3-(2-methoxyphenyl)-1,1-dimethylpropyl]amino]-1-ethanol		C₂₇H₃₃NO₃	详情	详情
(IV)	31696	2-[4-(benzyloxy)phenyl]-2-oxoacetaldehyde; 4-benzyloxy-alpha-oxophenylacetaldehyde		C₁₅H₁₂O₃	详情	详情
(V)	36427	1-[4-(benzyloxy)phenyl]-2-[[3-(2-methoxyphenyl)-1,1-dimethylpropyl]imino]-1-ethanone		C₂₇H₂₉NO₃	详情	详情
(VI)	36423	1-[4-(benzyloxy)phenyl]-1-ethanone	54696-05-8	C₁₅H₁₄O₂	详情	详情

Extended Information