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【结 构 式】

【分子编号】36805

【品名】(2-methoxyethoxy)methyl 3-[(2R)oxiranyl]phenyl ether; (2R)-2-[3-[(2-methoxyethoxy)methoxy]phenyl]oxirane

【CA登记号】

【 分 子 式 】C12H16O4

【 分 子 量 】224.25664

【元素组成】C 64.27% H 7.19% O 28.54%

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:(VI)

3-Hydroxybenzaldehyde (I) was protected as the methoxyethoxymethyl ether derivative (II) by treatment with methoxyethoxymethyl chloride and diisopropyl ethyl amine. Subsequent condensation of (II) with dimethyloxosulfonium methylide, generated from oxosulfonium salt (III) and NaH, gave rise to the racemic epoxide (IV). Kinetic resolution by hydrolysis with (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt (III) acetate complex provided the (S)-diol (V) along with the unreacted (R)-epoxide (VI), which were separated by column chromatography. Opening of the desired (R)-epoxide (VI) with methanolic methylamine gave amino alcohol (VII). Finally, removal of the methoxyethoxymethyl group by refluxing in methanolic HCl furnished the title compound.

1 Gurjar, M.K.; et al.; A practical synthesis of (R)-(-)-phenylephrine hydrochloride. Org Process Res Dev 1998, 2, 6, 422.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
11021 Methanamine; Methylamine 74-89-5 CH5N 详情 详情
40670 2-(chloromethoxy)ethyl methyl ether; 1-(chloromethoxy)-2-methoxyethane; (2-methoxyethoxy)methyl chloride 3970-21-6 C4H9ClO2 详情 详情
(I) 28537 3-hydroxybenzaldehyde 100-83-4 C7H6O2 详情 详情
(II) 36802 3-[(2-methoxyethoxy)methoxy]benzaldehyde C11H14O4 详情 详情
(III) 29693 Trimethylsulfoxonium iodide 1774-47-6 C3H9IOS 详情 详情
(IV) 36803 (2-methoxyethoxy)methyl 3-(2-oxiranyl)phenyl ether; 2-[3-[(2-methoxyethoxy)methoxy]phenyl]oxirane C12H16O4 详情 详情
(V) 36804 (1S)-1-[3-[(2-methoxyethoxy)methoxy]phenyl]-1,2-ethanediol C12H18O5 详情 详情
(VI) 36805 (2-methoxyethoxy)methyl 3-[(2R)oxiranyl]phenyl ether; (2R)-2-[3-[(2-methoxyethoxy)methoxy]phenyl]oxirane C12H16O4 详情 详情
(VII) 36806 (1R)-1-[3-[(2-methoxyethoxy)methoxy]phenyl]-2-(methylamino)-1-ethanol C13H21NO4 详情 详情
Extended Information