Ethyl Acetate → HCID 76846474, compound

Participants

Reaction Conditions

Reaction Steps

0.26 g of sodium cyanoborohydride is gradually added to a solution of 0.44 g of 4-(2-methoxyphenyl)indole in 5 ml of trifluoroacetic acid under argon, cooled to a temperature of about −5° C. The reaction mixture is stirred at a temperature of about −5° C. for 2 hours, and is then poured into 15 g of ice and alkalinized with 8 ml of a concentrated sodium hydroxide solution. After the addition of 30 ml of ethyl acetate, the mixture is stirred at ambient temperature for 1 hour, and then separated by settling out. The organic phase is separated and the aqueous phase is extracted with 15 ml of ethyl acetate. The organic phases are combined, dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is treated again with a mixture of 15 ml of water, 15 ml of ethyl acetate and 3 ml of a concentrated sodium hydroxide solution and stirred at ambient temperature for 15 minutes, and then separated by settling out. The organic phase is separated and the aqueous phase is extracted with 2×15 ml of ethyl acetate. The organic phases are combined, dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is purified by chromatography on a 25 g cartridge of 15-40 μm silica, elution being carried out with pure dichloromethane, at a flow rate of 30 ml/min. 0.14 g of 4-(2-methoxyphenyl)-2,3-dihydro-1H-indole is thus obtained in the form of an off-white solid, the characteristics of which are the following:

Provenance & Evidence