반응 #51501

반응 방정식

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

용매

methanol

반응 조건

후처리

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

실험 절차

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.

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