Acetic Acid → 2-(3,4-dichlorophenyl)-1-{(4aRS,8SR,8aRS)-4-[(1H-imidazol-5-yl)methyl]-8-(pyrrolidin-1-yl)perhydroquinoxalin-1-yl}ethan-1-one

Participants

Reaction Steps

2-(3,4-Dichlorophenyl)-1-[(4aRS,8SR,8aRS)-8-(pyrrolidin-1-yl)-perhydroquinoxalin-1-yl]-ethan-1-one (134 mg, 0.34 mmol) was dissolved in absolute CH2Cl2 (10 ml), and 1H-imidazole-5-carbaldehyde (65 mg, 0.67 mmol), NaBH(OAc)3 (143 mg, 0.67 mmol) and glacial acetic acid (41 mg, 0.67 mmol) were added. The mixture was stirred at room temperature for 2.5 hours. The mixture was then filtered and the organic phase was extracted by shaking three times with HCl (1 N). The aqueous phase was brought to pH 8 with NaOH (2 N) and extracted by shaking three times with CH2Cl2. The organic phases were dried over Na2SO4 and evaporated in vacuo. The residue was purified by preparative HPLC (as described under Example 14 in MeOH/H2O/Et2NH 80:20:0.1). MeOH was evaporated off from the product fraction, the aqueous phase was extracted by shaking three times with CH2Cl2 and the combined organic phases were dried over Na2SO4 and evaporated. A colorless solid was isolated.

Provenance & Evidence