Water → HCID 65041612, compound

Participants

Reaction Conditions

Reaction Steps

1.0 g of sodium cyanoborohydride is gradually added to a solution of 1.25 g of 2-cyclopropylindole in 80 ml of acetic acid under argon cooled to a temperature of about 15° C. The reaction mixture is stirred at a temperature of about 15° C. for 2 hours, and is then treated with 100 ml of water. It is then cooled to a temperature of about 5° C. and alkalinized by gradual addition of 140 ml of a 30% sodium hydroxide solution. The reaction mixture is diluted with 200 ml of ethyl acetate and is then stirred at ambient temperature for 15 hours. After settling out, the organic phase is separated and the aqueous phase is extracted with 3×200 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 taken up in a mixture of 60 ml of ethyl acetate, 40 ml of water and 10 ml of concentrated sodium hydroxide, and then the mixture is stirred at ambient temperature for 10 minutes. After settling out, the organic phase is separated and the aqueous phase is extracted with 2×50 ml of ethyl acetate. The organic phases are combined, dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. 1.2 g of (±)-2-cyclopropylindoline are thus obtained in the form of a brown oil which is used as it is.

Provenance & Evidence