Reaktion #51501

Reaktionsgleichung

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

→

title compound

(2S,3S)-3-amino-1-chloro-4-(3,5-difluorophenyl)butan-2-ol

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith heating at 50° for 2 hr
2. 2
   workup.WAITleft in the mixture
3. 3
   SonstigeThe reaction contents
4. 4
   Filtrationare filtered through a sintered funnel
5. 5
   Waschenthe resin washed with methanol (25 mL) and methanol/methylene chloride (1/1, 25 mL)
6. 6
   WaschenThe resulting mixture is eluted with ammonia in methanol (2N, 2×25 mL)
7. 7
   EinengenThe eluate is concentrated under reduced pressure

Vorschrift

tert-butyl (1S,2S)-3-chloro-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate (IV, EXAMPLE 3, 1.0 gm, 2.98 mmol) and Dowex50WX2-400 resin (4.6 gm 23.8 mmol) and methanol (25 mL) are mixed. The mixture is then placed over a J-Kim shaker with heating at 50° for 2 hr. ESMS analysis indicates no starting material left in the mixture. The reaction contents are filtered through a sintered funnel and the resin washed with methanol (25 mL) and methanol/methylene chloride (1/1, 25 mL). The resulting mixture is eluted with ammonia in methanol (2N, 2×25 mL). The eluate is concentrated under reduced pressure to give the title compound, ESMS=236.1.

Quelle