アミノ酸誘導体と生物活性(第2報)フェニルアラニンから2-アミノ-1-インダノール誘導体の合成
1979 年 99 巻 11 号 p. 1111-1115
詳細
1979 年 99 巻 11 号 p. 1111-1115
N-Phthaloyl-D, L-phenylalanine was converted to 2-phthalimido-1-indanone (3). Reduction of 3 with sodiumborohydride gave undesired compounds, 5 and 6. Compound 3 was hydrolyzed to give an aminoketone (4) which was reduced to cis- and trans-amino-indanols (7a and 7b). The reduction condition was examined to obtain cis-isomer (7a). The reductive N-alkylation of 7a with carbonyl compounds by sodium cyanoborohydride gave 2-alkylamino- or aralkylamino-1-indanols (8-12) which were shown to be inactive for antibacterial and β-adrenergic blocking effects. The phthaloylphenylalanyl chloride (2) was treated with aluminum chloride in benzene to give 14, which was reduced to the corresponding alcohol (15).
