Skatole → 3-Methylindoline

Participants

Reaction Steps

Under a nitrogen atmosphere 0.58 g (9.2 mmol) sodium cyanoborohydride were added batchwise to 1.0 g (7.6 mmol) 3-methylindole in 5.0 mL glacial acetic acid and the mixture was stirred for 60 min at RT. Then the reaction mixture was poured onto a 4N aqueous sodium hydroxide solution and extracted with EtOAc. The combined organic phases were washed several times with saturated sodium hydrogen carbonate solution, dried on sodium sulphate and evaporated down.

Provenance & Evidence