Tetrabutylammonium Fluoride → 4-(5-Oxazol-5-yl-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester
反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[O:55][C:35]3=[CH:36][N:37]=[C:38]([C:40]4[O:44][C:43]([Si](C(C)C)(C(C)C)C(C)C)=[N:42][CH:41]=4)[CH:39]=[C:34]3[CH:33]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O1CCCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([C:32]2[O:55][C:35]3=[CH:36][N:37]=[C:38]([C:40]4[O:44][CH:43]=[N:42][CH:41]=4)[CH:39]=[C:34]3[CH:33]=2)[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]参加物
4
反応物 2
生成物 1
試薬・触媒・溶媒 1
実験手順
Tetrabutylammonium fluoride (1 mol/L in tetrahydrofuran; 1.5 mL) is added to a solution of 4-[5-(2-triisopropylsilanyl-oxazol-5-yl)-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.31 g) in tetrahydrofuran (6 mL) chilled in an ice bath. The cooling bath is removed and the solution is stirred at room temperature for 2 h. Water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4) and concentrated. The residue is purified by HPLC on reversed phase (methanol/water) to give the title compound. LC (method 4): tR=1.66 min; Mass spectrum (ESI+): m/z=370 [M+H]+.