Methyl chloroglyoxylate → HCID 59408989, compound

Participants

Reaction Conditions

Reaction Steps

A solution 8-bromo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline (9.53 g, 40.0 mmol) in anhydrous tetrahydrofuran (317 ml) cooled to −78° C. was treated with n-butyllithium (36.1 ml, 90.1 mmol; 2.5M solution in hexanes) then stirred for 20 minutes. The reaction was treated with copper (I) cyanide (10.88 g, 120.1 mmol) then allowed to warm to between 0 and 10° C. before cooling back to −78° C. Methyl chlorooxoacetate (11.1 ml, 120.7 mmol) was added and the mixture was allowed to warm to room temperature. Water (250 ml) was added to the reaction and then the reaction was basified with saturated aqueous sodium bicarbonate. Dichloromethane (200 ml) was added and the mixture was filtered through a bed of celite. The organic layer was removed and the aqueous layer was extracted with dichloromethane (2×200 ml). The combined organic layers were dried with anhydrous sodium sulfate and evaporated to dryness to give a dark green oil which was purified by flash column chromatography (SiO2, 20% EtOAc in hexanes to 25% EtOAc in hexanes) to afford oxo-(1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-8-yl)-acetic acid methyl ester as a yellow/brown solid (8.4 g). M.p=102-105° C.; 400 MHz 1H NMR (CDCl3) δ: 7.55 (s, 1H), 7.50 (s, 1H), 3.92 (s, 3H), 3.58 (t, 2H), 3.19 (m, 2H), 3.01 (t, 2H), 2.66 (t, 2H), 2.02 (m, 2H); LCMS: 246 [M+H].

Provenance & Evidence