반응 #48688

반응 방정식

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

용매

ethyl acetate

반응 조건

후처리

1. 1
   기타Add methanol to quench
2. 2
   기타the reaction (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 (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).

출처