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【结 构 式】

【分子编号】35254

【品名】1-[2-(2-thienyl)ethyl]-4-piperidinol

【CA登记号】

【 分 子 式 】C11H17NOS

【 分 子 量 】211.32812

【元素组成】C 62.52% H 8.11% N 6.63% O 7.57% S 15.17%

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:(III)

A total synthesis of sufentanil has been described: The cyclization of 2-(2-thienyl)ethylamine (I) with allyltrimethylsilane (II) and formaldehyde gives 4-hydroxy-1-[2-(2-thienyl)ethyl]piperidine (III), which is oxidized with oxalyl chloride in DMSO/dichloromethane to 1-[2-(2-thienyl)ethyl]piperidin-4-one (IV). The epoxidation of (IV) by means of trimethylsulfonium iodide and the sodium salt of DMSO yields the spiro-epoxide (V), which is opened with aniline (VI) and boron trifluoride ethearate giving a 1.8:1 mixture of 4-(hydroxymethyl)-4-(phenylamino)piperidine (VII) and 4-hydroxy-4-(phenylamino)piperidine (VIII) that are conveniently separated. The methylation of the OH group of (VII) with diazomethane and SiO2 affords the methoxymethyl compound (IX), which is finally acylated with propionic anhydride to provide sufentanil.

1 Park, H.J.; Jeon, R.O.; Ryu, J.S.; Hyun, S.S.; Suh, Y.G.; Shin, D.Y.; Total synthesis of sufentanil. Arch Pharmacal Res 1999, 22, 4, 398.
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) 35253 2-(2-thienyl)ethylamine; 2-(2-thienyl)-1-ethanamine; 2-Thiophene ethylamine 30433-91-1 C6H9NS 详情 详情
(II) 15775 Allyltrimethylsilane; allyl(trimethyl)silane 762-72-1 C6H14Si 详情 详情
(III) 35254 1-[2-(2-thienyl)ethyl]-4-piperidinol C11H17NOS 详情 详情
(IV) 35255 1-[2-(2-thienyl)ethyl]-4-piperidinone C11H15NOS 详情 详情
(V) 35256 6-[2-(2-thienyl)ethyl]-1-oxa-6-azaspiro[2.5]octane C12H17NOS 详情 详情
(VI) 12294 Aniline; Phenylamine 62-53-3 C6H7N 详情 详情
(VII) 35257 [4-anilino-1-[2-(2-thienyl)ethyl]-4-piperidinyl]methanol C18H24N2OS 详情 详情
(VIII) 35258 4-(anilinomethyl)-1-[2-(2-thienyl)ethyl]-4-piperidinol C18H24N2OS 详情 详情
(IX) 35259 N-[4-(methoxymethyl)-1-[2-(2-thienyl)ethyl]-4-piperidinyl]-N-phenylamine; 4-(methoxymethyl)-N-phenyl-1-[2-(2-thienyl)ethyl]-4-piperidinamine C19H26N2OS 详情 详情
Extended Information