tert-butyl 3-formyl-1H-indole-1-carboxylate → HCID 86590908、化合物
反応式
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=O)=[CH:9]1)=O)(C)(C)C.[BH-](O[C:29]([CH3:31])=[O:30])(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:12]1([CH3:13])[CH:11]=[CH:10][CH:9]=[CH:31][C:29]=1[O:30][C:14]1[CH:15]=[C:16]2[C:11]([CH2:17][CH2:10][CH2:9][NH:8]2)=[CH:12][CH:13]=1参加物
4
実験手順
A mixture of 3-formyl-indole-1-carboxylic acid t-butyl ester, Compound 9, where R1 is 4-tolyl, R2 is H, R3 is 2-methylprop-1-yl, and R4 is CH3 (9 mg (0.0609 mmol) and NaBH(OAc)3 (17 mg, 0.0812 mmol) in 1 mL of anhydrous CH2Cl2 was vigorously stirred for 2 days, during which the the initially cloudy solution turned clear. The mixture was partitioned between 5 mL of EtOAc and 3 mL of saturated-NH4Cl solution and extracted three times. The combined EtOAc layer was washed with brine, dried over Na2SO4 and evaporated to dryness under vacuum. The product was purified by a silica gel column with Hexane/EtOAc (4/1-2/1) to afford 15 mg of 7-tolyloxy-3,4-dihydro-2H-quinoline-1-(3-methyl-indole-3-yl-1-carboxylic acid t-butyl ester)-4-spiro-5′-3′-1(2-methylpropy-1-yl)-1′ methyl-imidazolidine-2′,4′-dione as a light brown oil (71% yield).