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【结 构 式】

【分子编号】20768

【品名】methyl 2-(4-ethyl-3,5-dimethoxyphenyl)acetate

【CA登记号】

【 分 子 式 】C13H18O4

【 分 子 量 】238.28352

【元素组成】C 65.53% H 7.61% O 26.86%

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:(IV)

The reaction of benzaldehyde (I) with the sulfoxide (II) by means of benzyltrimethylammonium hydroxide in methanol gives the styrene derivative (III), which is hydrolyzed with HCl in methanol to the phenylacetate (IV). The condensation of (IV) with dimethyl oxalate by means of NaH in THF yields the succinate (V), which by reaction with formaldehyde and K2CO3 is converted into the acrylate (VI). The condensation of (VI) with ethyl 3-(methylamino)propionate gives intermediate (VII), which is cyclized by means of NaH in refluxing toluene yielding the piperidinone (IX). The condensation of (IX) with trimethyl phosphonoacetate (X) by means of NaH in THF affords the expected piperidinyleneacetate (XI), which is reduced with H2 over Pd/C in methanol giving the piperidinylacetate (XII). The cyclization of (XII) by means of polyphosphoric acid (PPA) in refluxing toluene yields the benzoisoquinoline (XIII), which is finally selectively demethylated with BBr3 in methylene chloride to the target compound.

1 Stadler, H.; Bos, M.; Wichmann, J. (F. Hoffmann-La Roche AG); Tricyclic benzo[e]isoindoles and benzo[h]isoquinolines . EP 0958285; JP 2000507965; WO 9830546 .
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) 20754 4-ethyl-3,5-dimethoxybenzaldehyde C11H14O3 详情 详情
(II) 20766 methyl (methylsulfanyl)methyl sulfoxide; methyl[(methylsulfanyl)methyl]oxo-lambda(4)-sulfane 33577-16-1 C3H8OS2 详情 详情
(III) 20767 methyl (Z)-2-(4-ethyl-3,5-dimethoxyphenyl)-1-(methylsulfanyl)-1-ethenesulfenate C14H20O3S2 详情 详情
(IV) 20768 methyl 2-(4-ethyl-3,5-dimethoxyphenyl)acetate C13H18O4 详情 详情
(V) 20769 dimethyl 2-(4-ethyl-3,5-dimethoxyphenyl)-3-oxosuccinate C16H20O7 详情 详情
(VI) 20770 methyl 2-(4-ethyl-3,5-dimethoxyphenyl)acrylate C14H18O4 详情 详情
(VII) 20771 ethyl 3-(methylamino)propanoate C6H13NO2 详情 详情
(VIII) 20772 methyl 3-[(3-ethoxy-3-oxopropyl)(methyl)amino]-2-(4-ethyl-3,5-dimethoxyphenyl)propanoate C20H31NO6 详情 详情
(IX) 20773 3-(4-ethyl-3,5-dimethoxyphenyl)-1-methyl-4-piperidinone C16H23NO3 详情 详情
(X) 13272 Methyl 2-(dimethoxyphosphoryl)acetate; Trimethyl phosphoroacetate 5927-18-4 C5H11O5P 详情 详情
(XI) 20775 methyl 2-[3-(4-ethyl-3,5-dimethoxyphenyl)-1-methyl-4-piperidinylidene]acetate C19H27NO4 详情 详情
(XII) 20776 methyl 2-[3-(4-ethyl-3,5-dimethoxyphenyl)-1-methyl-4-piperidinyl]acetate C19H29NO4 详情 详情
(XIII) 20777 (4aR,10bS)-8-ethyl-7,9-dimethoxy-2-methyl-1,3,4,4a,5,10b-hexahydrobenzo[h]isoquinolin-6(2H)-one C18H25NO3 详情 详情
Extended Information