Aminoacetaldehyde dimethyl acetal → HCID 22141244, compound

Participants

Reaction Steps

To a solution of ethyl 3-(3-hexyl-6-methyl-2-oxo-3-azabicyclo[3.1.0]hex-6-yl)benzenecarboximidoate hydrochloride (Preparation 42, 528 mg, 1.45 mmol) in methanol (6 ml) at room temperature was added aminoacetaldehyde dimethylacetal (0.16 g, 1.52 mmol). The mixture was heated under reflux for 90 min, cooled to room temperature and the solvent was removed in vacuo. The crude residue was dissolved in 6N hydrochloric acid (8 ml) and the mixture was heated to 80° C. for 30 min and then left at room temperature for 2 h. The mixture was diluted with water (5 ml), the pH was adjusted to 9 using 5N sodium hydroxide solution and the aqueous solution was extracted with ethyl acetate (3×20 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude residue was purified by silica column chromatography eluting with ethyl acetate:methanol:ammonia solution (0.880) (90:10:1) to afford the title compound (190 mg, 39%) as a colourless oil.

Provenance & Evidence