Reaktion #51492

Reaktionsgleichung

tert-butyl (1S,2S)-3-chloro-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate

potassium hydroxide

water

→

title compound

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

Lösungsmittel

ethanol

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 250 mL 3-neck round bottom flask equipped with magnetic stir bar, nitrogen inlet
2. 2
   Temperaturcooled to 0°
3. 3
   Temperaturthe resulting suspension is warmed to 15-20°
4. 4
   Sonstigethe reaction contents
5. 5
   Temperaturare cooled to −5°
6. 6
   workup.STIRRINGstirred for 30 min
7. 7
   FiltrationThe solids are collected by filtration
8. 8
   Waschenwashed with cold water (2×25 mL)
9. 9
   Sonstigethen dried under reduced pressure at 450

Vorschrift

To a 250 mL 3-neck round bottom flask equipped with magnetic stir bar, nitrogen inlet and thermocouple, is added tert-butyl (1S,2S)-3-chloro-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate IV, EXAMPLE 3, 3.5 g, 0.010 moles, 1 equivalent) followed by absolute ethanol (60 mL) and cooled to 0°. To this mixture is added potassium hydroxide (0.73 g, 0.013 moles, 1.25 equivalents) dissolved in absolute ethanol (10 mL) over 1 hr and the resulting suspension is warmed to 15-20° and stirred for 1 hr. At this time, water (100 mL) is added and the reaction contents are cooled to −5° and stirred for 30 min. The solids are collected by filtration and washed with cold water (2×25 mL) then dried under reduced pressure at 450 to give the title compound, mp=133°; NMR (DMSO-d6) δ 7.03, 3.61, 2.68-2.98 and 1.33; CMR (DMSO-d6) δ 163.72, 161.29, 155.55, 143.35, 112.65, 101.80, 78.17, 53.42, 52.71, 44.90, 36.98 and 28.36.

Quelle