Acetic Acid → HCID 67491863, compound

Participants

Reaction Steps

2-Methyl-1-aza-bicyclo[2.2.2]octan-3-one (500 mg, 3.59 mmol) and 2,4-dimethoxybenzyl amine (1.2 g, 7.18 mmol) were dissolved in anhydrous 1,2-dichloroethane (10 ml). Sodium triacetoxyborohydride (1.1 g, 5.0 mmol) followed by glacial acetic acid (0.21 ml, 3.59 mmol) and the resultant foamy suspension was stirred at ambient temperature for 12 hours. The reaction was quenched by the addition of 1M NaOH, and the layers were separated. The aqueous phase was extracted further with ethyl acetate. The organic portions were combined, dried (Na2SO4), filtered and concentrated in vacuo. The crude reaction mixture was purified by chromatography [eluent gradient: 10-30% MeOH/Et3N (9:1) in EtOAc) to give pure (2,4-dimethoxy-benzyl)-(2-methyl-1-aza-bicyclo[2.2.2]oct-3-yl)-amine.

Provenance & Evidence