1,2-Dichloroethane → HCID 11949417, compound

Participants

Reaction Steps

(+)-(1R,3R)-3-Amino-1-(3-chloro-phenylethynyl)-cyclohexanol (115 mg, 0.46 mmol) was dissolved in DMF (5 ml) and treated with furan-3-carboxylic acid ((63 mg, 0.55 mmol) and EDC (108 mg, 0.55 mmol). After stirring for 1.5 h at room temperature, Et3N (0.55 mmol) was added and stirring continued for 18 h. A second batch of EDC (108 mg, 0.55 mmol) was added and stirring continued for 6 h. EtOAc was added and the mixture washed with aqueous sodium bicarbonate and brine. Drying of the organic phase with Na2SO4, filtration and evaporation afforded a crude product (263 mg) which was purified by chromatography on silica gel to afford the title compound as a white solid (105 mg, 66%). MS (LC/MS): 344.2 [M+H]; [α]D=+95.6° (c=0.5, MeOH).

Provenance & Evidence