Reaktion #1135452

Reaktionsgleichung

(5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-3-(2-(triisopropylsilyloxy)ethyl)piperidin-2-one

(5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-3-(2-(triisopropylsilyloxy)ethyl)piperidin-2-one

sodium periodate

→

2-((5R,6S)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-2-oxo-3-(2-(triisopropylsilyloxy)ethyl)piperidin-3-yl)acetaldehyde

Lösungsmittel

THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationwas filtered through a fitted funnel
2. 2
   EinengenThe filtrate was partially concentrated under reduced pressure
3. 3
   workup.ADDITIONwas diluted with water
4. 4
   Extraktionextracted with ethyl acetate (2×)
5. 5
   WaschenThe combined organic layers were washed with saturated aqueous sodium thiosulfate
6. 6
   TrocknenThe organic layer was dried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Einengenthe filtrate was concentrated

Vorschrift

To a solution of 1.28 g (2.08 mmol) of (5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-(cyclopropylmethyl)-3-(2-(triisopropylsilyloxy)ethyl)piperidin-2-one (Example 69, Step A, mixture of diastereomers) in THF (50 mL) and water (17.5 mL) was added a catalytic amount of osmium tetroxide. After 25 min, 1.34 g (6.25 mmol) of sodium periodate was added. The resulting light brown slurry was stirred for 19 h and then was filtered through a fitted funnel. The filtrate was partially concentrated under reduced pressure, then was diluted with water and extracted with ethyl acetate (2×). The combined organic layers were washed with saturated aqueous sodium thiosulfate and then saturated aqueous sodium chloride. The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated. The crude title compound (mixture of C-3 epimers) was used directly in the next step.

Quelle