تفاعل #48688

معادلة التفاعل

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

المذيبات

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىAdd methanol to quench
2. 2
   أخرىthe reaction (1.0 mL)
3. 3
   workup.STIRRINGstir vigorously for 30 minutes
4. 4
   أخرىSeparate the organic layer
5. 5
   استخلاصextract the aqueous with ethyl acetate
6. 6
   تجفيفdry (magnesium sulfate)
7. 7
   ترشيحfilter
8. 8
   تركيزconcentrate

الإجراء التجريبي

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).

المصدر