Reaktion #1349032

Reaktionsgleichung

Et3N

Dimethyl sulfoxide

oxalyl chloride

(3S,5S)-3-allyl-5-hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester

→

title compound

Ausbeute 111.8%

(3S,5S)-3-Allyl-5-formyl-morpholine-4-carboxylic acid tert-butyl ester

Ausbeute 111.8%

Lösungsmittel

DCM

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeafter 20 min the ice bath was removed
2. 2
   WaschenAfter 30 min the reaction mixture was washed with sat. aq. sodium hydrogencarbonate solution
3. 3
   WaschenThe organic layer was washed with brine
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated

Vorschrift

Dimethyl sulfoxide (498 mg, 6.38 mmol) was added at −70° C. to a solution of oxalyl chloride (405 mg, 3.19 mmol) in DCM (5 mL), then after 15 min a solution of (3S,5S)-3-allyl-5-hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester (547 mg, 2.13 mmol) in DCM (3 mL) was added. The reaction mixture was stirred at −70° C. for 30 min, then treated with Et3N (1.29 g, 12.8 mmol), then after 20 min the ice bath was removed. After 30 min the reaction mixture was washed with sat. aq. sodium hydrogencarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to afford the title compound (608 mg) as a light yellow gum, which was directly used in the next step.

Quelle