반응 #48692

반응 방정식

diisobutylaluminum hydride

(3S,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-3-methylmorpholin-2-one

→

desired compound

수율 99.0%

(2RS,3S,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-3-methylmorpholin-2-ol

수율 99.0%

용매

toluene

반응 조건

후처리

1. 1
   기타Quench
2. 2
   workup.ADDITIONby adding methanol (1.0 mL)
3. 3
   workup.STIRRINGstir vigorously for 30 minutes
4. 4
   기타Separate the organic layer
5. 5
   추출extract the aqueous with ethyl acetate
6. 6
   건조dry (magnesium sulfate)
7. 7
   여과filter
8. 8
   농축concentrate

실험 절차

Add diisobutylaluminum hydride (2.48 mL, 2.48 mmol, 1.0 M in toluene) to a solution of (3S,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-3-methylmorpholin-2-one (1.09 g, 1.91 mmol) in dry toluene (20 mL) at −78° C. under nitrogen and stir at this temperature for 15 minutes. Quench by adding methanol (1.0 mL). Add saturated aqueous potassium sodium tartrate (Rochelle salt) and ethyl acetate, warm to room temperature and stir vigorously for 30 minutes. Separate the organic layer and extract the aqueous with ethyl acetate. Combine the organic layers, dry (magnesium sulfate), filter and concentrate to give the desired compound as a mixture of the two possible epimers as a white solid which is used directly in the next step without further purification (1.08 g, 99% yield).

출처