[N+:1]1([O-])[CH:6]=[CH:5][CH:4]=[C:3]2[CH:7]([C:10]([O:12][CH3:13])=[O:11])[CH2:8][CH2:9][C:2]=12.C([NH2:19])(C)(C)C.C1(C)C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[NH2:19][C:6]1[N:1]=[C:2]2[CH2:9][CH2:8][CH:7]([C:10]([O:12][CH3:13])=[O:11])[C:3]2=[CH:4][CH:5]=1To a solution of methyl 6,7-dihydro-5H-cyclopenta[b]pyridine-5-carboxylate 1-oxide (700 mg, 3.6 mmol) in CF3-toluene (20 mL) and CHCl3 (20 mL) was added tert-butylamine (3.8 mL, 36 mmol). The solution was cooled to 0° C. in an ice bath. To the solution was added p-toluenesulfonic anhydride (3.5 g, 10.9 mmol) in small portions until all SM was consumed according to LC-MS. The volatiles were removed under reduced pressure, and the residue was redissolved in TFA (20 mL). The solution was heated to 70° C. for 2 hours. The reaction was stopped at that point. TFA was removed on a rotavapor, and the residue was taken up in saturated sodium carbonate, and extracted three times with IPA-CHCl3 (1:3, 50 mL each). The extractions were combined, dried over sodium sulfate, adsorbed onto silica gel, and purified by MPLC (DCM:MeOH with 10% aq NH4OH). After removal of solvent the title compound was collected: LC-MS (IE, m/z): 193 [M+1]+.
読み込み中…
