Reaktion #49189

Reaktionsgleichung

sucrose

ketoester

1-(6-Benzyloxycarbonylamino-hexanoyl)-4-oxo-pyrrolidine-3-carboxylic acid ethyl ester

sucrose

→

alcohol

Ausbeute 42.3%

1-(6-Benzyloxycarbonylamino-hexanoyl)-4-hydroxy-pyrrolidine-3-carboxylic acid ethyl ester

Ausbeute 42.3%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe content of the flask was then poured into a flask
2. 2
   workup.DISTILLATIONdistilled water
3. 3
   workup.ADDITIONwas added
4. 4
   workup.WAITAfter 48 h
5. 5
   Filtrationthe suspension was filtered through a pad of Celite
6. 6
   WaschenThe pad was washed with water
7. 7
   Extraktionthe aqueous layer was extracted with ethyl acetate (3×250 mL)
8. 8
   TrocknenThe combined organic layer was dried over anhydrous sodium sulfate
9. 9
   Filtrationfiltered
10. 10
    Einengenconcentrated under reduced pressure

Vorschrift

To a solution of sucrose (3 g) in distilled water (40 mL) was added Baker's yeast (2 g). The suspension was heated at 32° C. for 1 h. The content of the flask was then poured into a flask containing ketoester 60 (4 g, 9.88 mmol, dissolved in 4 mL of methanol). Stirring was continued at 32° C. for 24 h after which additional sucrose (3 g) in warm (40° C.) distilled water was added. After 48 h, the suspension was filtered through a pad of Celite. The pad was washed with water and the aqueous layer was extracted with ethyl acetate (3×250 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to flash chromatography (30% EtOAc/Hexane) to afford alcohol 62 (1.7 g, 42%).

Quelle