【结 构 式】 |
【分子编号】48991 【品名】N-[(3S)-1-benzylpyrrolidinyl]-1-adamantanecarboxamide 【CA登记号】 |
【 分 子 式 】C22H30N2O 【 分 子 量 】338.49308 【元素组成】C 78.06% H 8.93% N 8.28% O 4.73% |
合成路线1
该中间体在本合成路线中的序号:(III)Condensation of (S)-3-amino-1-benzylpyrrolidine (I) with 1-adamantanecarbonyl chloride (II) by means of Et3N in dichloromethane affords amide (III), which is then debenzylated by hydrogenolysis over Pd/C and hydrazine monohydrate to provide amine (IV). Subsequent N-alkylation of (IV) with tosylate (V) in acetonitrile in the presence of K2CO3 furnishes the corresponding alylated compound (VI), which is finally converted into the desired hydrochloride monohydrate derivative by first treatment with HCl:isopropanol in ethyl acetate followed by recrystallization in EtOH:H2O using activated carbon.
【1】 Kuroita, T.; Sakai, Y.; Fujio, M.; Nakagawa, H.; Matsumoto, Y.; N-[1-(2-phenylethyl)pyrrolidin-3-yl]-1-adamantanecarboxamides as novel 5-HT2 receptor antagonists. Bioorg Med Chem Lett 2000, 10, 21, 2457. |
【2】 Kuroita, T.; Nakagawa, H.; Fujio, M. (Welfide Corporation); Pyrrolidine cpds. and medicinal utilization thereof. EP 1125922; WO 0026186 . |
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) | 48990 | (S)-N-Benzyl-3-aminopyrrolidine; (3S)-(+)-1-Benzyl-3-aminopyrrolidine; (3S)-(+)-N-Benzyl-3-amino pyrrolidine | 114715-38-7 | C11H16N2 | 详情 | 详情 |
(II) | 31216 | 1-adamantanecarbonyl chloride | 2094-72-6 | C11H15ClO | 详情 | 详情 |
(III) | 48991 | N-[(3S)-1-benzylpyrrolidinyl]-1-adamantanecarboxamide | C22H30N2O | 详情 | 详情 | |
(IV) | 48992 | N-[(3R)pyrrolidinyl]-1-adamantanecarboxamide | C15H24N2O | 详情 | 详情 | |
(V) | 45818 | 2-(4-fluorophenyl)-1-ethanamine; 4-fluorophenethylamine | C8H10FN | 详情 | 详情 | |
(VI) | 48993 | N-[(3R)-1-(4-fluorophenethyl)pyrrolidinyl]-1-adamantanecarboxamide | C23H31FN2O | 详情 | 详情 |