Sodium Carbonate → HCID 54212612, compound

Participants

Reaction Conditions

Reaction Steps

Trans-4-benzyl-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinolin-7-carbaldehyde (1.4 g, 4.59 mmol), ethyl azidoacetate (2.7g, 20.9 mmol), diethyl ether (10 ml), and methanol (30 ml) were cooled to -5° C. (Henn et al., J. Chem. Soc. Perkin Trans. I, 1984, 2189-2196). Sodium methoxide (3.89 ml, 18.4 mmol, of a 25% w/w solution in methanol) was slowly added. The reaction was allowed to reach ambient temperature and stirred for 1 hr. The mixture was cooled to 0° C. and saturated aqueous ammonium chloride added. The reaction was rapidly partioned between ether and 10% aqueous sodium carbonate. The ethereal layer was washed with water and brine and the resulting organic phase dried (magnesium sulfate) and evaporated to dryness. The residue was used without any further purifications (1.85 g, 100%).

Provenance & Evidence