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【结 构 式】 
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【分子编号】52140 【品名】ethyl (3R)-1-[3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-3-piperidinecarboxylate 【CA登记号】 |
【 分 子 式 】C26H31NO2 【 分 子 量 】389.53768 【元素组成】C 80.17% H 8.02% N 3.6% O 8.21% |
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)Addition of cyclopropylmagnesium bromide (II) to dibenzocycloheptanone (I) afforded the carbinol adduct (III), which was further rearranged to the bromopropylidene derivative (IV) upon treatment with bromotrimethylsilane. Alkylation of ethyl (R)-nipecotate (V) with bromide (IV) gave the tertiary amine (VI). The ethyl ester group of (VI) was finally hydrolyzed under basic conditions to furnish the corresponding carboxylic acid.
| 【1】 Andersen, K.E.; Olsen, U.B.; Petersen, H.; Grønvald, F.C.; Sonnewald, U.; Jørgensen, T.K.; Andersen, H.S. (Novo Nordisk A/S); Novel heterocyclic cpds.. US 5595989; US 5668129; US 5688788; US 5693649; US 5712292; US 5721254; US 5795888; US 6043239; WO 9518793 . |
| 【2】 Olsen, U.B. (Novo Nordisk A/S); Novel method. JP 1999507947; WO 9722338 . |
| 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) | 40123 | 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one; Dibenzosuberone | 1210-35-1 | C15H12O | 详情 | 详情 |
| (II) | 12450 | Bromo(cyclopropyl)magnesium;cyclopropylmagnesium bromide;cyclopropylmagnesiumbromide | 23719-80-4 | C3H5BrMg | 详情 | 详情 |
| (III) | 52138 | 5-cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol | C18H18O | 详情 | 详情 | |
| (IV) | 52139 | 5-(3-bromopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene | C18H17Br | 详情 | 详情 | |
| (V) | 35224 | ethyl (3S)-3-piperidinecarboxylate | C8H15NO2 | 详情 | 详情 | |
| (VI) | 52140 | ethyl (3R)-1-[3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-3-piperidinecarboxylate | C26H31NO2 | 详情 | 详情 |
Extended Information