Phosphorus oxychloride → HCID 86618849, compound

Participants

Reaction Conditions

Reaction Steps

Crude 4-(2-hydroxy-7-methoxy-quinolin-4-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (3.18 g, 7.60 mmol) was dissolved in POCl3 (76 mL) and heated to 40° C. overnight. The reaction mixture was concentrated in vacuo and dissolved in CH2Cl2 (40 mL). 4 N HCl in 1,4-dioxane (40 mL) was added and stirred at r.t. for 1 h. The crude material was partitioned between H2O and CH2Cl2 and pH was adjusted to 11 with NaHCO3 and 1 N NaOH. The aqueous layer was extracted with CH2Cl2 (3×150 mL). The combined organic layer was dried with Na2SO4 and concentrated. The crude product was purified by combi-flash to give 2.05 g of 4-(2-Chloro-7-methoxy-quinolin-4-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester.

Provenance & Evidence