Réaction #48692

Équation de réaction

diisobutylaluminum hydride

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

→

desired compound

Rendement 99.0%

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

Rendement 99.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   AutreQuench
2. 2
   workup.ADDITIONby adding methanol (1.0 mL)
3. 3
   workup.STIRRINGstir vigorously for 30 minutes
4. 4
   AutreSeparate the organic layer
5. 5
   Extractionextract the aqueous with ethyl acetate
6. 6
   Séchagedry (magnesium sulfate)
7. 7
   Filtrationfilter
8. 8
   Concentrationconcentrate

Mode opératoire

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).

Source