tert-Butyl (4-methylpyridin-3-yl)carbamate → HCID 45092184, Verbindung
Reaktionsgleichung
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]>C(O)(=O)C.O=[Pt]=O>[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Tert-butyl 4-methylpyridin-3-ylcarbamate (200 mg, 0.96 mmol) was dissolved in glacial acetic acid (5 mL) and treated with PtO2 (200 mg, 1:1 w/w) under an atmosphere of hydrogen. The reaction mixture was stirred at rt for 15 h. The reaction mixture was then filtered through a pad of Celite. The filtrate was neutralized with solid NaHCO3, and extracted with EtOAc (5×50 mL). The organic layer was dried over Na2SO4, concentrated in vacuo to yield the titled compound (160 mg, 77%), which was used for next step without further purification. 1H NMR (400 MHz, CDCl3): δ 4.38-4.21 (m, 1H), 3.32-2.81 (m, 3H), 2.63-2.49 (m, 2H), 2.41-2.32 (m, 1H), 1.78-1.56 (m, 3H), 1.59 (s, 9H), 1.05 and 0.98 (2d, J=6.8 Hz, 3H). ES-MS: m/z [M+1]=215.