Benzyl Bromide → HCID 69953258, compound

Participants

Reaction Steps

Trimethylsilyl trifluoromethanesulfonate (1.30 mL, 6.76 mmol) was added dropwise to a cold (0° C.) solution of the piperidine formed in step b (0.819 g, 1.69 mmol) and 2,6-lutidine (0.590 mL, 5.07 mmol) in CH2Cl2 (17 mL). After 1.5 hours, saturated sodium bicarbonate (NaHCO3) was added and the resulting mixture was stirred at room temperature for 15 min. The white precipitate formed was collected by filtration and redissolved in water at pH 2. This acidic aqueous layer was extracted with CH2Cl2 (2 times) and EtOAc (1 time). All organic layers were combined, dried (MgSO4), filtered, and concentrated. The crude white solid obtained was suspended in THF (30 mL) and DMF (50 mL), and triethylamine (0.40 mL, 2.86 mmol) and benzyl bromide (0.22 mL, 1.86 mmol) were added. The resulting heterogenous mixture was stirred at room temperature for 24 hours (with time a more homogenous mixture was obtained). The mixture was concentrated, and CH2Cl2 was added to the residue. The organic layer was washed with water and brine and dried (MgSO4), filtered, and concentrated. Purification by silica gel flash chromatography (CH2Cl2 →5% MeOH/CH2Cl2) gave the title compound (free base) (0.334 g, 49%) as a white foam.

Provenance & Evidence