Dichloromethane → 4-(1-methanesulfonyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 300 mg of 4-(1-hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (see Example 5) and 10 mL of methylene chloride was cooled to 0° C. To this mixture, 0.060 mL of methanesulfonyl chloride and 0.204 mL of triethylamine were added. The reaction mixture was allowed to stir at the same temperature for 30 minutes. The reaction was worked up by adding water, and the product was extracted with EtOAc three times. The organic layers were combined, washed sequentially with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution, water, and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo to give 344 mg of 4-(1-methanesulfonyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester as a solid, which was used for the next coupling reaction without further purification.

Provenance & Evidence