Reaktion #168136

Reaktionsgleichung

Na2CO3

(S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-{(S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-ethyl}-1,3-oxazinan-2-one

5-bromo-pyridine-2-carboxylic acid methyl ester

→

title compound

5-(4-{(S)-1-[(S)-6-(2-Hydroxy-2-methyl-propyl)-2-oxo-6-phenyl-[1,3]oxazinan-3-yl]-ethyl}-phenyl)-pyridine-2-carboxylic acid

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II)dichloromethane complex (61 mg)
2. 2
   workup.ADDITIONwas added
3. 3
   TemperaturAfter cooling to ambient temperature
4. 4
   workup.ADDITIONthe mixture was diluted with ethyl acetate
5. 5
   Extraktionextracted with water and brine
6. 6
   Extraktionextracted with CH2Cl2/MeOH (ca. 10:1)
7. 7
   WaschenThe combined organic extracts were washed with brine
8. 8
   Trocknendried (MgSO4)
9. 9
   SonstigeThe solvent was removed
10. 10
    Sonstigethe residue was purified by chromatography on silica gel (CH2Cl2/MeOH 98:2→50:50)

Vorschrift

2 M aqueous Na2CO3 solution (1.3 mL) was added to a solution of (S)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-3-{(S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-ethyl}-1,3-oxazinan-2-one (0.60 g) and 5-bromo-pyridine-2-carboxylic acid methyl ester (0.41 g) in N,N-dimethylformamide (4 mL). The resulting mixture was sparged with argon for 10 min, before [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II)dichloromethane complex (61 mg) was added. The mixture was heated to 100° C. and stirred at this temperature overnight. After cooling to ambient temperature, the mixture was diluted with ethyl acetate and extracted with water and brine. The aqueous extracts were combined, acidified (pH ca. 5-6) using citric acid, and extracted with CH2Cl2/MeOH (ca. 10:1). The combined organic extracts were washed with brine and dried (MgSO4). The solvent was removed and the residue was purified by chromatography on silica gel (CH2Cl2/MeOH 98:2→50:50) to afford the title compound as a resin-like solid.

Quelle