Reaktion #48688

Reaktionsgleichung

potassium sodium tartrate

diisobutylaluminum hydride

(R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-oxomorpholine-4-carboxylic acid tert-butyl ester

toluene

→

desired compound

(R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-hydroxymorpholine-4-carboxylic acid tert-butyl ester

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAdd methanol to quench
2. 2
   Sonstigethe reaction (1.0 mL)
3. 3
   workup.STIRRINGstir vigorously for 30 minutes
4. 4
   SonstigeSeparate the organic layer
5. 5
   Extraktionextract the aqueous with ethyl acetate
6. 6
   Trocknendry (magnesium sulfate)
7. 7
   Filtrationfilter
8. 8
   Einengenconcentrate

Vorschrift

Add diisobutylaluminum hydride (1.4 mL, 1.37 mmol, 1.0 M in toluene) to a solution of (R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-oxomorpholine-4-carboxylic acid tert-butyl ester (0.75 g, 1.1 mmol) in of dry toluene (15 mL) at −78° C. under nitrogen and stir at this temperature for 2 hours (Monitor by TLC). Add methanol to quench the reaction (1.0 mL), then 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 and dry (magnesium sulfate), filter and concentrate to give the desired compound as a mixture of the two possible isomers as a white solid and used in the next step without further purification (0.75 g).

Quelle