[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH:19]1([CH2:24][C:25](Cl)=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20]1>C(Cl)Cl>[CH:19]1([CH2:24][C:25]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH2:8][C:9]3=[O:12])=[CH:4][CH:3]=2)=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20]1To a mixture of 7-amino-1-tetralone (13.2 g) (prepared as described above and used without further purification) and pyridine (8.4 ml) in methylene chloride (130 ml) at 0° C. was added a solution of cyclopentylacetyl chloride (13.2 g) in methylene chloride (20 ml). The reaction was stirred for 30 min and at room temperature for 1.5 h. The mixture was evaporated and the residue was diluted with ethyl acetate, washed (saturated sodium bicarbonate, 1N HCl, brine), dried (MgSO4) and evaporated. The residue was flash chromatographed, eluting with ethyl acetate:methylene chloride (5:95, 7.5:92.5, and 1:9, successively), to give 7-cyclopentylacetamido-1-tetralone (16.6 g, 74%) as a colorless solid; mp 117.0°-118.0° C.
Loading…
