1,1-Dimethylethyl N-[(1R,6S)-6-azido-2,2-difluorocyclohexyl]carbamate → HCID 58046449, Verbindung
Reaktionsgleichung
[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]1[C@@H:13]([N:14]=[N+]=[N-])[CH2:12][CH2:11][CH2:10][C:9]1([F:18])[F:17])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6](=[O:19])[NH:7][C@@H:8]1[C@@H:13]([NH2:14])[CH2:12][CH2:11][CH2:10][C:9]1([F:18])[F:17])([CH3:4])([CH3:2])[CH3:3]Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of tert-butyl[(1R,6S)-6-azido-2,2-difluorocyclohexyl]carbamate (18.84 g, 68.2 mmol) in methanol (400 mL) was degassed and purged (3× with N2) before the addition of Pd/C (1.45 g). The reaction was stirred for 2 d under 1 atm of hydrogen. Upon reaction completion, the reaction was filtered through a plug of celite and concentrated to dryness to afford the title compound as a white solid. 1H NMR (CDCl3, 500 MHz) 4.76-4.74 (d, 1H); 3.61-3.56 (m, 1H); 2.63-2.59 (dd, 1H); 2.2-2.0 (m, 2H); 1.8-1.68, (m, 2H); 1.53-1.42 (m, 11H); 1.29-1.21 (m, 2H). 19F NMR (CDCl3, 564 MHz) −101.7-−102.1 (d, 1F); −114.3-−114.9 (m, 1F).