Reaktion #42362

Reaktionsgleichung

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

3-isopropylbenzylamine hydrochloride

→

title compound

tert-Butyl (1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-[(3-isopropylbenzyl)amino]propylcarbamate

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction is cooled
2. 2
   EinengenThe solution is concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONredissolved in chloroform
4. 4
   Waschenwashed with 1N hydrochloric acid, saturated sodium bicarbonate, brine
5. 5
   Trocknendried (sodium sulfate)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigePurification by flash chromatography (silica, 7% methanol/chloroform)

Vorschrift

tert-Butyl (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiran-2-yl]ethylcarbamate (2.0 g, 6.7 mmol) and 3-isopropylbenzylamine hydrochloride (2.5 g, 13.5 mmol) in isopropanol (60 mL) are refluxed 3 h. The reaction is cooled and stirred 16 h. The solution is concentrated under reduced pressure, redissolved in chloroform, washed with 1N hydrochloric acid, saturated sodium bicarbonate, brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. Purification by flash chromatography (silica, 7% methanol/chloroform) gives the title compound in pure form. ESI MS m/z 449.3 [M+H]+.

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