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【结 构 式】

【分子编号】33806

【品名】ethyl 5,5-dimethyl-3-oxooctanoate

【CA登记号】

【 分 子 式 】C12H22O3

【 分 子 量 】214.30488

【元素组成】C 67.26% H 10.35% O 22.4%

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:(I)

Condensation of ketoester (I) with nitrovinyl benzodioxole (II) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene gave adduct (III). Hydrogenation of the nitro group of (III) over Raney Nickel with concomitant cyclization yielded dihydropyrrole (IV). Further reduction of (IV) with sodium cyanoborohydride provided a mixture of diastereomeric pyrrolidines. Chromatographic separation removed the cis,cis isomer, affording a mixture of trans,trans and cis,trans products (V). N-Alkylation of the pyrrolidine (V) with N,N-dibutyl bromoacetamide (VI) furnished (VIIa-b). Finally, selective hydrolysis of the ester group from the trans,trans isomer produced a mixture of cis,trans ester (VIII) and the target trans,trans acid, which were readily separated by fractional extraction.

1 Winn, M.; Boyd, S.A.; Hutchins, C.W.; Tasker, A.S.; Von Geldern, T.W.; Kester, J.A.; Sorensen, B.K.; Szczepankiewicz, B.G.; Henry, K.J. Jr.; Liu, G.; Wittenberger, S.J.; King, S.A. (Abbott Laboratories Inc.); Novel benzo-1,3-dioxolyl- and benzofuranyl substd. pyrrolidine derivs. as endothelin antagonists. EP 0885215; WO 9730045 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(Va) 33810 ethyl (2S,3R,4S)-2-(2,2-dimethylpentyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)-3-pyrrolidinecarboxylate C22H33NO5 详情 详情
(Vb) 33811 ethyl (2R,3R,4S)-2-(2,2-dimethylpentyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)-3-pyrrolidinecarboxylate C22H33NO5 详情 详情
(VIIa) 33812 ethyl (2S,3R,4S)-1-[2-(dibutylamino)-2-oxoethyl]-2-(2,2-dimethylpentyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)-3-pyrrolidinecarboxylate C32H52N2O6 详情 详情
(VIIb),(VIII) 33813 ethyl (2R,3R,4S)-1-[2-(dibutylamino)-2-oxoethyl]-2-(2,2-dimethylpentyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)-3-pyrrolidinecarboxylate C32H52N2O6 详情 详情
(I) 33806 ethyl 5,5-dimethyl-3-oxooctanoate C12H22O3 详情 详情
(II) 33807 4-methoxy-6-[(E)-2-nitroethenyl]-1,3-benzodioxole; methyl 6-[(E)-2-nitroethenyl]-1,3-benzodioxol-4-yl ether C10H9NO5 详情 详情
(III) 33808 ethyl 2-[1-(7-methoxy-1,3-benzodioxol-5-yl)-2-nitroethyl]-5,5-dimethyl-3-oxooctanoate C22H31NO8 详情 详情
(IV) 33809 ethyl 2-(2,2-dimethylpentyl)-4-(7-methoxy-1,3-benzodioxol-5-yl)-4,5-dihydro-1H-pyrrole-3-carboxylate C22H31NO5 详情 详情
(VI) 20685 2-Bromo-N,N-dibutylacetamide; N,N-Dibutylbromoacetamide C10H20BrNO 详情 详情
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