Trifluoroacetic acid → 6-(3-Aminopyrrolidin-1-yl)nicotinonitrile
반응식
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH:15]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][N:21]=2)[CH2:16]1)(C)(C)C>ClCCl>[NH2:14][CH:15]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][N:21]=2)[CH2:16]1참가 물질
4
실험 절차
Add trifluoroacetic acid (30 mL) to [1-(5-cyanopyridin-2-yl)-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (7.95 g, 27.6 mmol) in dichloromethane (200 mL) and stir for 2 h. Concentrate, add toluene (100 mL) and reconcentrate to give a residue. Partition the residue between dichloromethane and an saturated aqueous solution of sodium bicarbonate and separate the layers. Extract the aqueous layer 5 times with 15:85 isopropyl alcohol:chloroform, combine the organic layers, dry (sodium sulfate), filter, and concentrate to give the title compound as a yellow oil (5.25 g). 1H NMR (400 MHz, CDCl3) δ 8.34 (d, 1H, J=2.5 Hz), 7.53-7.50 (m, 1H), 6.29 (d, 1H, J=8.8 Hz), 3.80-3.10 (m, 5H), 2.25-2.15 (m, 1H), 1.90-1.75 (m, 3H); MS (ES): m/z=189 [M+H]+.