Ethanol → HCID 9841901, compound

Participants

Reaction Steps

Sodium borohydride (3.2 g) was added in portions at 0° C. under nitrogen to a stirred solution of 1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-[3-(dimethylamino)-propylthio]ethanone (16 g, prepared by basification of the hydrochloride salt obtained in a similar manner to that described in Example 7) in methanol (200 ml) then the mixture was stirred at ambient temperature for 7 days and diluted with water (350 ml). The product was extracted into dichloromethane (4×100 ml) and the extracts washed with water (100 ml) and saturated aqueous sodium chloride solution (100 ml), dried over sodium sulphate and the solvent removed in vacuo to leave a green oil. The oil was resolved via preparative scale chiral high performance liquid chromatography to give (-)-1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-[3 -(dimethylamino)propylthio]ethanol as an oil (3.5 g), [α]rtD =-8.615° (C=1;ethanol) and (+)-1-[1-(3 4-dichlorophenyl)cyclobutyl]-2-[3-(dimethylamino) propylthio]ethanol as an oil (3.4 g), [α]rtD =+9.740° (C=1; ethanol).

Provenance & Evidence