HCID 57475162, compound → HCID 57475061, compound

Participants

Reaction Steps

(±)-Methyl 2-(2-(4-(dimethylamino)-4-phenylcyclohex-1-enyl)-1H-indol-3-yl)acetate (936 mg, 2.4 mmol) was dissolved in HBr/glacial acetic acid (33% HBr, 30 ml). Sn powder (2.88 g, 24 mmol) was then added to the mixture in portions at RT in the course of 1 h. When the addition had ended, the reaction mixture was stirred at RT for a further 16 h.—For working up, the mixture was diluted with EtOH (10 ml) and concentrated to dryness on a rotary evaporator. The residue which remained was rendered basic by addition of 2 N NaOH (100 ml). The aqueous mixture obtained was extracted with methylene chloride (4×40 ml). The combined organic phases were dried over Na2SO4 and then concentrated. The crude product obtained (900 mg) was purified by column chromatography [silica gel 60 (100 g); MeOH (1,000 ml)] Methyl 2-(2-(4-(dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)acetate (less polar diastereomer) was obtained in a yield of 290 mg (31%), and the polar diastereomer was obtained in a yield of 200 mg (21%). Both products were colourless oils.

Provenance & Evidence