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【结 构 式】

【分子编号】40447

【品名】(1R,2R)-2-chlorocyclohexanol

【CA登记号】1561-86-0

【 分 子 式 】C6H11ClO

【 分 子 量 】134.60544

【元素组成】C 53.54% H 8.24% Cl 26.34% O 11.89%

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:(V)

By refluxing a solution of equimolecular quantities of 3-pentyloxyphenyl isocyanate (I) and trans-2-(1-pyrrolidinyl)cyclohexanol (II) in toluene. The obtained pentacaine base is transformed to the hydrochloride by treatment of an ether solution of anhydrous hydrogen chloride (1,2). The starting amino-alcohol (II) is prepared from cyclohexanol (III), which is first dehydrated to cyclohexene (IV). The following addition of HClO gives trans-2-chlorocyclohexanol (V), which, in turn is dehydrochlorinated to 1,2-epoxycyclohexane (VI). Final addition of pyrrolidine (A) yields the required intermediate (II).

1 Castaner, J.; Pentacaine. Drugs Fut 1976, 1, 8, 379.
2 Subert, J.; et al.; Studies on local anesthetics. XLVIII. Preliminary analytical evaluation of the substance K-1902 (pentacaine). Cesk Farm 1975, 24, 5.
3 Benes, L.; Borovansky, A.; Kopácová, L.; Basische trans- und cis-Cyklohexylester substituierter Alkoxycarbanilsäuren. XLI. Studien über Lokalanästhetika. Arch Pharm 1972, 305, 648.
4 Benes, L.; Borovansky, A.; Kopácová, L.; Alkoxycarbanilic acid esters with high local anaesthetic activity. Arzneim-Forsch Drug Res 1969, 19, 1902-3.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 11376 Pyrrolidine 123-75-1 C4H9N 详情 详情
(I) 14636 3-(pentyloxy)phenyl isocyanate; 1-isocyanato-3-(pentyloxy)benzene C12H15NO2 详情 详情
(II) 14637 (1R,2R)-2-(1-pyrrolidinyl)cyclohexanol C10H19NO 详情 详情
(III) 11306 Cyclohexanol 108-93-0 C6H12O 详情 详情
(IV) 40446 1-cyclohexene 110-83-8 C6H10 详情 详情
(V) 40447 (1R,2R)-2-chlorocyclohexanol 1561-86-0 C6H11ClO 详情 详情
(VI) 40448 (1R,6R)-7-oxabicyclo[4.1.0]heptane C6H10O 详情 详情
Extended Information