Reaktion #1977617

Reaktionsgleichung

oxa-5-azaspiro[2.3]hexane-5-carboxylic acid tert-butyl ester

7-methoxy-2(1H)-quinolinone

Cs2CO3

→

title intermediate

Ausbeute 10.0%

3-hydroxy-3-(7-methoxy-2-oxo-2H-quinolin-1-ylmethyl)-azetidine-1-carboxylic acid tert-butyl ester

Ausbeute 10.0%

Lösungsmittel

DMF

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed under reduced pressure
2. 2
   Sonstigethe residue was partitioned between water and EA
3. 3
   ExtraktionThe aq. layer was extracted with EA
4. 4
   Trocknenlayers were dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   Sonstigepurified by CC (DCM-MeOH 19:1 to 9:1)

Vorschrift

A solution of oxa-5-azaspiro[2.3]hexane-5-carboxylic acid tert-butyl ester (69 mg; prepared according to WO 2007/044515) in DMF (1 mL) was added to a suspension of 7-methoxy-2(1H)-quinolinone (60 mg; commercial) and Cs2CO3 (223 mg, 2 eq.) in DMF (2 mL). The reaction mixture was stirred at 80° C. for 10 days. The solvent was removed under reduced pressure and the residue was partitioned between water and EA. The aq. layer was extracted with EA. The combined org. layers were dried over Na2SO4, filtered, evaporated and purified by CC (DCM-MeOH 19:1 to 9:1) to afford the title intermediate as a yellow oil (12 mg, 10% yield).

Quelle