Reaktion #72226

Reaktionsgleichung

Dess-Martin reagent

methyl 5-((3R*,4S*)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-3-(1-hydroxyethyl)thiophene-2-carboxylate

Methyl 5-((3R*,4S*)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-3-(1-hydroxyethyl)thiophene-2-carboxylate

sodium thiosulfate

→

title compound

Ausbeute 49.5%

Methyl cis(±)-3-acetyl-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)thiophene-2-carboxylate

Ausbeute 49.5%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGby stirring at room temperature
2. 2
   ExtraktionThen, the mixture was extracted with chloroform
3. 3
   TrocknenThe combined organic layers were dried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltration
5. 5
   Einengenthe filtrate was concentrated under reduced pressure
6. 6
   SonstigeThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1)

Vorschrift

The Dess-Martin reagent (305 mg, 0.72 mmol) was added to a solution of methyl 5-((3R*,4S*)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-3-(1-hydroxyethyl)thiophene-2-carboxylate obtained in Example (246d) (215 mg, 0.48 mmol) in dichloromethane (5 mL) at room temperature, followed by stirring for one hour. Aqueous sodium thiosulfate solution was added to the reaction solution, followed by stirring at room temperature. Then, the mixture was extracted with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate. Following filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/1) to obtain 106 mg of the title compound as a yellow oily substance (50%).

Quelle