Acetic Acid → HCID 69652704, compound

Participants

Reaction Conditions

Reaction Steps

0.22 ml (3.12 mmol) of DMSO in 2 ml of 1,2-dichlorethane is added in drops to a solution of 0.18 ml (2.04 mmol) of oxalyl chloride in 4 ml of 1,2-dichloroethane at −70° C. After 10 minutes at −70° C., a solution of 270 mg (1.02 mmol) of 8-chloro-7-hydroxyethyl-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one in 5 ml of 1,2-dichloroethane and 2 ml of DMSO are added in drops to it. After 2 hours at −70° C., the batch is diluted with 30 ml of dichloromethane and stirred for 3 hours at −70° C. After 1.27 ml (9.18 mmol) of triethylamine is added, the reaction solution is stirred for 1 hour at room temperature and concentrated by evaporation in a vacuum. The residue is taken up in 20 ml of 1,2-dichloroethane and 20 ml of THF and mixed with 0.14 ml (1.53 mmol) of 3-chlorobenzylamine, 323 mg (1.53 mmol) of sodium (triacetoxy)borohydride and 0.6 ml (10.2 mmol) of acetic acid. After 24 hours at room temperature, the batch is diluted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with dichloromethane-methanol yields 220 mg of product.

Provenance & Evidence