Acetic Acid → HCID 44241901, compound

Participants

Reaction Steps

4-(dimethylamino)-4-phenylcyclohexanone (1.1 g, 5.41 mmol) was dissolved in a mixture of 1,2-dichloroethane (30 ml) and tetrahydrofuran (40 ml) in argon, mixed with (S)-2-amino-3-(1H-indol-3-yl)-N,N-dimethylpropanamide (1 g, 4.3 mmol), acetic acid (0.31 ml, 5.41 mmol) and Na2SO4 (2.7 g). The mixture was stirred for 15 min at RT and then mixed with sodium triacetoxyboron hydride (1.65 g, 7.57 mmol) and stirred for 48 hours. For work up of the batch the mixture was mixed with saturated NaHCO3 solution (60 ml) and stirred for 15 min. The aqueous phase was extracted with dichloromethane (2×40 ml). The combined organic phases were concentrated to low volume after drying and a light brown oil was obtained. The chromatographic separation of the substance mixture on silica gel 60 (100 g) was conducted with ethyl acetate/methanol (1:1).

Provenance & Evidence