Reaktion #561112

Reaktionsgleichung

NEt3

3-[(S)-1-(4-bromo-phenyl)-ethyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one

dimethylformamide

MeOH

→

title compound

4-{(S)-1-[(S)-6-(2-Hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-benzoic acid methyl ester

Lösungsmittel

MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting mixture was sparged with argon for 5 min
2. 2
   Sonstigetransferred to a pressure-proved vessel
3. 3
   workup.ADDITIONthat was filled with CO (5.5. bar)
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGAfter stirring at 70° C. for another 4 h
6. 6
   Temperaturthe mixture was cooled to ambient temperature
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated under reduced pressure
9. 9
   Waschenthe resulting mixture was washed with water and brine
10. 10
    Trocknendried (MgSO4)
11. 11
    SonstigeThe solvent was removed
12. 12
    Sonstigethe residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 40:60->0:100)

Vorschrift

NEt3 (0.47 mL) and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) dichloromethane complex (0.15 g) were added to a solution of 3-[(S)-1-(4-bromo-phenyl)-ethyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one (1.04 g) in MeCN (2.5 mL), MeOH (20 mL), and dimethylformamide (5 mL). The resulting mixture was sparged with argon for 5 min and then transferred to a pressure-proved vessel that was filled with CO (5.5. bar). The mixture was heated to 70° C. and stirred at this temperature for 18 h before another portion of [1,1′-bis(diphenyl-phosphino)ferrocene]-dichloropalladium(II) dichloromethane complex (0.15 g) was added. After stirring at 70° C. for another 4 h, the mixture was cooled to ambient temperature, filtered, and concentrated under reduced pressure. The residue was taken up in ethyl acetate and the resulting mixture was washed with water and brine and dried (MgSO4). The solvent was removed and the residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 40:60->0:100) to afford the title compound as an oil.

Quelle