Tetrahydrofuran → HCID 67407238, compound

Participants

Reaction Steps

2-(aminomethyl)-4-(3-fluorophenyl)-N,N-dimethyl-4′,9′-dihydro-3′H-spiro[cyclohexane-1,1′-pyrano[3,4-b]indole]-4-amine (130 mg, 0.31 mmol) was dissolved in absolute tetrahydrofuran (20 ml) with argon. Hünig's base (0.1 ml, 0.63 mmol) and cinnamic acid chloride (105 mg, 0.63 mmol) dissolved in absolute tetrahydrofuran (8 ml) were added one after the other to the clear solution at room temperature. After a reaction time of 45 min, the batch was mixed with water (10 ml) and 2 N sodium hydroxide solution (10 ml) and stirred for 1 h. For work up tetrahydrofuran was distilled off completely. The aqueous mixture was extracted with dichloromethane (3×20 ml). The combined organic extracts were washed once again with water (20 ml), dried over Na2SO4 and concentrated to low volume. The raw product (247 mg) was separated by chromatography [silica gel 60 (30 g); ethyl acetate/cyclohexane 5:1 (600 ml)]. One of four possible diastereoisomers was obtained as white solid with a yield of 108 mg (65%) and with a melting point of 134-140° C.

Provenance & Evidence