Reaktion #1983053

Reaktionsgleichung

isoquinoline

t-BuOK

N-BOC-4-hydroxy-L-proline

potassium t-butoxide

citric acid

→

title compound

1-N-BOC-4-(6-Methoxy-3-methylisoquinolin-1-yloxy)pyrrolidine-2-carboxylic acid

Lösungsmittel

DMSO

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthen cooled to 0° C
2. 2
   Temperaturto warm up to RT
3. 3
   workup.STIRRINGThe solution was stirred for 16 h
4. 4
   workup.ADDITIONan addition 0.2 equivalents of A
5. 5
   workup.ADDITIONwas added
6. 6
   workup.STIRRINGthe mixture stirred for an additional 1.5 h
7. 7
   ExtraktionThe solution was extracted with ethyl acetate
8. 8
   Waschenthe organic phase washed with water
9. 9
   EinengenThe organic phase was concentrated in vacuo

Vorschrift

N-BOC-4-hydroxy-L-proline (A; 281 mg; 1.21 mmol) was dissolved in DMSO (3 mL) at RT then potassium t-butoxide (270 mg; 2.4 mmol) was added. The resulting solution was stirred at RT for 2 h then cooled to 0° C. Next a solution of isoquinoline 14 in DMSO (3 mL) was added dropwise to the cold solution of A and t-BuOK, then the mixture was allowed to warm up to RT. The solution was stirred for 16 h, and an addition 0.2 equivalents of A was added and the mixture stirred for an additional 1.5 h. The reaction mixture was acidified to pH=4 with 5% aq. citric acid. The solution was extracted with ethyl acetate and the organic phase washed with water followed by saturated aq. NaCl. The organic phase was concentrated in vacuo to give the title compound.

Quelle