Reaktion #308900

Reaktionsgleichung

K2CO3

HCl

2-[2-azido-2-(3-bromo-phenyl)-propoxy]-3,3,3-trifluoro-2-methyl-propionic acid methyl ester

indium

→

title compound

2-[2-amino-2-(3-bromo-phenyl)-propoxy]-3,3,3-trifluoro-2-methyl-propionic acid methyl ester

Lösungsmittel

THF H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe product was extracted with EtOAc
2. 2
   WaschenThe combined organic layers were washed with brine
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe crude product was purified by flash-chromatography on NEt3 deactivated silica gel (hexane/EtOAc 2:1 to EtOAc)
7. 7
   Sonstigeto provide

Vorschrift

To a solution of the 2-[2-azido-2-(3-bromo-phenyl)-propoxy]-3,3,3-trifluoro-2-methyl-propionic acid methyl ester (4.2 g, 9.22 mmol) in THF-H2O 3:1 (48 ml) was added indium (2.116 g, 18.43 mmol) followed by 4N aqueous HCl over a period of 20 min and stirring for 1 h at 25° C. The reaction mixture was added to a 10% aqueous K2CO3 solution and the product was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated. The crude product was purified by flash-chromatography on NEt3 deactivated silica gel (hexane/EtOAc 2:1 to EtOAc) to provide a diastereomeric mixture of the title compound as a yellow oil: TLC (EtOAc): Rf=0.46; HPLC RtH5=0.999 min; 1H NMR (360 MHz, CDCl3): δ 7.73 (s, 1H), 7.47 (d, 1H), 7.41 (d, 1H), 7.24 (t, 1H), 3.84 and 3.83 (s, 3H), 3.59 (s, 2H), 1.61 and 1.59 (s, 3H), 1.52 and 1.51 (s, 3H); ESIMS: 384, 386 [(M+H)+].

Quelle