Propylamine → HCID 10469743, compound

Participants

Reaction Steps

To a mixture of 0.211 g (0.84 mmol) of the product of Step A and 0.177 g (2.94 mmol) of n-propylamine dissolved in 8 mL of CH2Cl2 was added 0.5 g of finely powdered 4 Å molecular sieves. The reaction mixture was stirred under a nitrogen atmosphere at room temperature overnight, then 0.445 g (2.1 mmol) of sodium triacetoxyborohydride was added. The reaction was then stirred an addition 8 h at room temperature, then diluted with CH2Cl2 and MeOH. The mixture was filtered through a pad of Celite filter aid eluted with CH2Cl2, and the filtrate was washed with saturated aqueous NaHCO3. The organic layer was the separated, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified on a silica gel flash chromatography column eluted first with CH2Cl2-MeOH—NH4OH (96:3:1) followed by CH2Cl2-MeOH—NH4OH (94:5:1). Evaporation of the purified fractions and drying in vacuo afforded the title compound.

Provenance & Evidence