Acetaldehyde → (S,S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-phenylethyl)amine

Participants

Reaction Steps

Sodium triacetoxyborohydride (26 grams, 0.123 mole) was added to a suspension of (S,S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-1-phenylethylamine hydrochloride (26 grams, 0.08 mole) in dichloroethane (300 ml) and triethylamine (11.5 ml). After stirring for 5 minutes, acetaldehyde (4.8 ml, 0.086 mole) was added and the mixture was stirred for another 2 hours. Aqueous 5% sodium carbonate (400 ml) was added and the mixture was extracted with methylene chloride. Evaporation of the solvent gave (S,S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-phenylethyl)amine as an oil (23 grams, 91%), M+ 309.

Provenance & Evidence