Acetic Acid → HCID 69652723, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 0.19 g (0.82 mmol) of 7-hydroxyethyl-1,2,3,3a,5,9b-hexahydro-cyclopenta[c]quinolin-4-one in 20 ml of dichloromethane is mixed at 0° C. with 0.38 g (0.90 mmol) of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277). The batch is stirred for 10 minutes at 0° C. and for 40 minutes at room temperature, diluted with dichloromethane (100 ml), washed with saturated NaHCO3 (30 ml), dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is dissolved in 1,2-dichloroethane (20 ml) and mixed with 0.11 ml (0.90 mmol) of 3-chlorobenzylamine, 0.30 g (1.40 mmol) of sodium (triacetoxy)borohydride and 0.05 ml (0.85 mmol) of acetic acid. After 20 hours at room temperature, the batch is diluted with ethyl acetate (150 ml), washed with water (2×50 ml), dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with dichloromethane-ethanol yields 69 mg of product.

Provenance & Evidence