Reaktion #308915

Reaktionsgleichung

(2R,5R)-5-(5-bromo-2-fluoro-phenyl)-2,5-dimethyl-2-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

sodium acetate

→

title compound

(2R,5R)-5-(2-Fluoro-phenyl)-2,5-dimethyl-2-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe catalyst was filtered off over Celite
2. 2
   Einengenthe filtrate was concentrated
3. 3
   workup.DISSOLUTIONThe residue was dissolved in saturated NaHCO3 solution
4. 4
   Extraktionextracted with EtOAc
5. 5
   WaschenCombined extracts were washed with brine
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

A solution of (2R,5R)-5-(5-bromo-2-fluoro-phenyl)-2,5-dimethyl-2-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine (1.66 g, 4.5 mmol) and sodium acetate (0.369 g, 4.5 mmol) in MeOH (50 ml) was hydrogenated over 10% Pd—C for 6 h at 50° C. The catalyst was filtered off over Celite and the filtrate was concentrated. The residue was dissolved in saturated NaHCO3 solution and extracted with EtOAc. Combined extracts were washed with brine, dried over MgSO4, filtered and concentrated to provide the title compound as a colorless oil: TLC (hexane-EtOAc 1:1): Rf=0.19; HPLC RtH5=0.777 min; ESIMS: 291 [(M+H)+]; 1H NMR (360 MHz, CDCl3): δ 7.41 (dt, 1H), 7.26 (m, 1H), 7.11 (t, 1H), 7.05 (dd, 1H), 4.11 (dd, 1H), 3.94 (dd, 1H), 1.54 (s, 3H), 1.49 (s, 3H).

Quelle