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【结 构 式】 
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【分子编号】53649 【品名】(1R)-N-[(E)-1-(1,3-benzodioxol-5-yl)butylidene]-1-phenyl-1-ethanamine; N-[(E)-1-(1,3-benzodioxol-5-yl)butylidene]-N-[(1R)-1-phenylethyl]amine 【CA登记号】n/a |
【 分 子 式 】C19H21NO2 【 分 子 量 】295.38128 【元素组成】C 77.26% H 7.17% N 4.74% O 10.83% |
合成路线1
该中间体在本合成路线中的序号：(XXXIX)The preferred synthetic route began with the Friedel-Crafts acylation of benzodioxol (XXXVII) by means of butyric anhydride and BF3. The resultant butyrophenone (XIII) was then condensed with (R)-1-phenylethylamine (XXXVII), using TiCl4 as the dehydrating reagent, to afford the E-imine (XXXIX) as the major isomer. Catalytic hydrogenation of imine (XXXIX) in the presence of Raney-Ni furnished the desired amine (XL). The chiral auxiliary was then removed by hydrogenolysis over Pd/C to yield amine (XVII).
| 【1】 Storace, L.; et al.; An efficient large-scale process for the human leukocyte elastase inhibitor, DMP 777. Org Process Res Dev 2002, 6, 1, 54. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIII) | 53629 | 1-(1,3-benzodioxol-5-yl)-1-butanone | 63740-97-6 | C11H12O3 | 详情 | 详情 |
| (XVII) | 53631 | (1R)-1-(1,3-benzodioxol-5-yl)-1-butanamine; (1R)-1-(1,3-benzodioxol-5-yl)butylamine | n/a | C11H15NO2 | 详情 | 详情 |
| (XXVIII) | 10039 | (1R)-1-Phenylethylamine; (1R)-1-Phenyl-1-ethanamine.; L-alpha-Phenylethylamine | 3886-69-9 | C8H11N | 详情 | 详情 |
| (XXXVII) | 50641 | 1,3-Dioxaindane; 1,3-Benzodioxole; methylenedioxybenzene; 1,2-methylenedioxybenzene; catechol methylene ether | 274-09-9 | C7H6O2 | 详情 | 详情 |
| (XXXIX) | 53649 | (1R)-N-[(E)-1-(1,3-benzodioxol-5-yl)butylidene]-1-phenyl-1-ethanamine; N-[(E)-1-(1,3-benzodioxol-5-yl)butylidene]-N-[(1R)-1-phenylethyl]amine | n/a | C19H21NO2 | 详情 | 详情 |
| (XL) | 53650 | N-[(1R)-1-(1,3-benzodioxol-5-yl)butyl]-N-[(1R)-1-phenylethyl]amine; (1R)-1-(1,3-benzodioxol-5-yl)-N-[(1R)-1-phenylethyl]-1-butanamine | n/a | C19H23NO2 | 详情 | 详情 |