Acetic Acid → HCID 59625185, compound

Participants

Reaction Steps

Methyl 3-[(tert-butoxycarbonyl)amino]-L-alaninate hydrochloride (2.00 g), 2-methylpropanal (860 μl) and acetic acid (450 μl) were dissolved in 1,2-dichloroethane-methanol (5:1, 60 ml), and the mixture was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (4.00 g) was added and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (0:1-1:0) was concentrated under reduced pressure to give the object compound (1.76 g).

Provenance & Evidence