Diisopropylethylamine → N-((R)-5-Bromoindan-2-yl)-4-butoxy-N-methylbenzamide

反応式

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@H:6]([NH2:11])[CH2:5]2.[CH:12](N(C(C)C)CC)(C)C.[CH2:21]([O:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)[CH2:22][CH2:23][CH3:24]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@H:6]([N:11]([CH3:12])[C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:26]([O:25][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:27][CH:28]=1)[CH2:5]2

参加物

実験手順

A mixture of (R)-5-bromoindan-2-ylamine (hydrochloride; 3.50 g), diisopropylethylamine (5.0 ml) and dichloromethane (20 ml) was admixed at 0° C. with 4-butoxybenzoyl chloride (3.00 g). After 30 minutes, the reaction mixture was partitioned between water and dichloromethane. The organic phase was concentrated and the residue was stirred with diethyl ether. The resulting amide was methylated on the amide nitrogen according to method D. This afforded the product with the molecular weight of 402.33 (C21H24BrNO2); MS (ESI): 402 (M+H+).