Reaktion #83800

Reaktionsgleichung

ethyl 2-azido-3-t-butyldimethylsilyloxy-3-(2-chloropyridin-3-yl)propionate

triphenylphosphine

tetrahydrofuran

→

title compound

Ausbeute 113.0%

Ethyl 2-amino-3-t-butyldimethylsilyloxy-3-(2-chloropyridin-3-yl)propionate

Ausbeute 113.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONAt the end of this time, the reaction mixture was freed from the solvent by distillation
2. 2
   SonstigeThe residue was purified by column chromatography through silica gel
3. 3
   workup.ADDITIONby volume mixture of hexane and ethyl acetate
4. 4
   workup.ADDITIONsubsequently a 50:1 by volume mixture of methylene chloride and methanol as the eluent

Vorschrift

A mixture of 5.6 g of ethyl 2-azido-3-t-butyldimethylsilyloxy-3-(2-chloropyridin-3-yl)propionate (prepared described in Preparation 77), 7.5 g of triphenylphosphine and 18 ml of a 8:1 by volume mixture of tetrahydrofuran and water was stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was freed from the solvent by distillation. The residue was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate and subsequently a 50:1 by volume mixture of methylene chloride and methanol as the eluent, to give 5.9 g of the title compound having Rf=0.59 (on silica gel thin layer chromatography using a 15:1 by volume mixture of methylene chloride and methanol as the developing solvent).

Quelle