Reaktion #42287

Reaktionsgleichung

Sodium azide

ammonium chloride

tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate

tert-Butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate

→

title compound

tert-Butyl-(1S,2R)-3-azido-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent is removed under reduced pressure
2. 2
   SonstigeThe concentrate is partitioned between ethyl acetate and water
3. 3
   Sonstigethe phases are separated
4. 4
   Waschenthe organic phase is washed with bicarbonate and saline
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated

Vorschrift

Sodium azide (0.22 g, 4 mmole) and ammonium chloride (2 eq) are added to tert-butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiranyl]ethylcarbamate (V, EXAMPLE 3, 0.6 g, 2 mmole). The reaction is heated to 75-80 degrees C. and stirred for 16 hours. The reaction is monitored by TLC to insure completion. The solvent is removed under reduced pressure. The concentrate is partitioned between ethyl acetate and water, the phases are separated and the organic phase is washed with bicarbonate and saline, dried over anhydrous sodium sulfate and concentrated to give the title compound, TLC (ethyl acetate/hexane) Rf=0.45; MS (MH+)=343.

Quelle