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【结 构 式】

【分子编号】61623

【品名】propyl 2-{(acetyloxy)[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutanoate

【CA登记号】

【 分 子 式 】C22H34O7

【 分 子 量 】410.50776

【元素组成】C 64.37% H 8.35% O 27.28%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IV)

The condensation of benzaldehyde (I) with ethyl isovalerate (II) by means of hexyl lithium and DIA in THF gives the hydroxyester (III), which is acylated with Ac2O and DMAP in THF to yield the acetoxy derivative (IV). The elimination reaction in (IV) by means of t-BuOK in THF affords the unsaturated ester (V), which is reduced with diisobutylaluminum hydride in toluene to provide the unsaturated alcohol (VI). Finally, this compound is enantioselectively reduced with H2 over a chiral biphenylyl diphenylphosphine catalyst and a [Rh(norbornadiene)Cl]2 catalyst in toluene to give the target intermediate 2(R)-isopropyl-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-1-propanol (VII). (see scheme 26758001d, intermediate (XXIX)).

1 Herold, P.; Stutz, S.; Spindler, F. (Speedel Pharma Inc.); Process for the preparation of (R)-2-alkyl-3-phenyl-1-propanols. WO 0202487 .
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) 61620 4-Methoxy-3-(3-methoxypropoxy)benzaldehyde 172900-75-3 C12H16O4 详情 详情
(II) 61621 propyl 3-methylbutanoate C8H16O2 详情 详情
(III) 61622 propyl 2-{hydroxy[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutanoate C20H32O6 详情 详情
(IV) 61623 propyl 2-{(acetyloxy)[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutanoate C22H34O7 详情 详情
(V) 61624 propyl (E)-2-isopropyl-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-propenoate C20H30O5 详情 详情
(VI) 61625 (E)-2-isopropyl-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-propen-1-ol C17H26O4 详情 详情
(VII) 50573 (2R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methyl-1-butanol C17H28O4 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 condensation of benzaldehyde (I) with ethyl isovalerate (II) by means of hexyl lithium and DIA in THF gives the hydroxyester (III), which is acylated with Ac2O and DMAP in THF to yield the acetoxy derivate (IV). The elimination reaction in (IV) by means of t-BuOK in THF affords the unsaturated ester (V), which is hydrolyzed with KOH in ethanol to provide the unsaturated free acid (VI). Finally, this compound is enantioselectively reduced with H2 over several chiral Rh catalysts {[Rh(NBD)2BF4, [Rh(NBD)(OCOCF3)2], [Rh(NBD)Cl2], etc} to give the target intermediate 2(R)-isopropyl-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]propionic acid (VII). (see scheme 26758001a, intermediate (VII)).

1 Herold, P.; Stutz, S. (Speedel Pharma Inc.); Preparation of (R)-2-alkyl-3-phenylpropionic acids. WO 0202500 .
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) 61620 4-Methoxy-3-(3-methoxypropoxy)benzaldehyde 172900-75-3 C12H16O4 详情 详情
(II) 61621 propyl 3-methylbutanoate C8H16O2 详情 详情
(III) 61622 propyl 2-{hydroxy[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutanoate C20H32O6 详情 详情
(IV) 61623 propyl 2-{(acetyloxy)[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutanoate C22H34O7 详情 详情
(V) 61624 propyl (E)-2-isopropyl-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-propenoate C20H30O5 详情 详情
(VI) 61626 (E)-2-isopropyl-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-propenoic acid C17H24O5 详情 详情
(VII) 28119 (2R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyric acid C17H26O5 详情 详情
Extended Information