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【结 构 式】

【分子编号】59251

【品名】methyl 3-chloro-4-cyclohexylbenzoate

【CA登记号】

【 分 子 式 】C14H17ClO2

【 分 子 量 】252.74048

【元素组成】C 66.53% H 6.78% Cl 14.03% O 12.66%

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:(XII)

A different synthetic strategy was further reported. Fischer esterification of 4-cyclohexylbenzoic acid (VIII) with MeOH and H2SO4, followed by aromatic nitration of the resultant benzoate ester (IX), yielded methyl 4-cyclohexyl-3-nitrobenzoate (X). Nitro group reduction in (X) by transfer hydrogenation provided amine (XI). This was converted to the chloro derivative (XII) by application of a modified Sandmeyer reaction with tert-butyl nitrite and cupric chloride. Ester group reduction in (XII) with LiBH4, followed by Swern oxidation of the resultant alcohol (XIII), furnished aldehyde (XIV). The aminoethyl phosphonium salt (XVI) was prepared by addition of N-ethyl cyclohexylamine (VI) to vinyl triphenylphosphonium bromide (XV). The corresponding ylide generated in situ from phosphonium salt (XV) and potassium bis(trimethylsilyl)amide was then subjected to a Wittig reaction with aldehyde (XIV) to afford the title (Z)-propenyl amine.

1 Burgess, L.E.; The preparation of immunosuppressant SR-31747. Synth Commun 1997, 27, 12, 2181.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 59245 N-Ethylcyclohexanamine; N-Ethylcyclohexylamine; Vulkacit HX 5459-93-8 C8H17N 详情 详情
(VIII) 59247 4-Cyclohexylbenzoic acid 20029-52-1 C13H16O2 详情 详情
(IX) 59248 4-Cyclohexylbenzoic acid methyl ester; Methyl 4-cyclohexylbenzoate 92863-34-8 C14H18O2 详情 详情
(X) 59249 methyl 4-cyclohexyl-3-nitrobenzoate C14H17NO4 详情 详情
(XI) 59250 methyl 3-amino-4-cyclohexylbenzoate C14H19NO2 详情 详情
(XII) 59251 methyl 3-chloro-4-cyclohexylbenzoate C14H17ClO2 详情 详情
(XIII) 59252 (3-chloro-4-cyclohexylphenyl)methanol C13H17ClO 详情 详情
(XIV) 59253 3-chloro-4-cyclohexylbenzaldehyde C13H15ClO 详情 详情
(XV) 59254 triphenyl(vinyl)phosphonium bromide C20H18BrP 详情 详情
(XVI) 59255 {2-[cyclohexyl(ethyl)amino]ethyl}(triphenyl)phosphonium bromide C28H35BrNP 详情 详情
Extended Information