Acetic Acid → 1-methylethyl [(cis)-1-acetyl-6-(4-{[(2-hydroxyethyl)amino]methyl}-1H-imidazol-1-yl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate

Participants

Reaction Steps

Dess-Martin periodinane (132 mg, 0.31 mmol) was added portionwise to a stirred suspension of 1-methylethyl {(cis)-1-acetyl-6-[4-(hydroxymethyl)-1H-imidazol-1-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (for a preparation see example 89) (100 mg, 0.26 mmol) in DCM (5 mL) and the resulting mixture was stirred at room temperature for 30 min. 5 mL of a saturated NaHCO3 aqueous solution was added and the mixture stirred for 15 min. The layers were separated and the aqueous phase was extracted with DCM (5 mL). The combined organic phases (DCM+AcOEt) were dried over MgSO4 and concentrated in vacuo. The residue was dissolved in DCM (5 mL) and Methanol (1 mL). Ethanolamine (63 mg, 1.03 mmol) and glacial acetic acid (15 mg, 15 μl, 0.26 mmol) were added. The reaction mixture was stirred at room temperature for 30 min then sodium triacetoxyborohydride (110 mg, 0.52 mmol) was added. The resulting mixture was stirred at room temperature for 16 h then treated with a saturated NaHCO3 aqueous solution. The layers were separated and the organic phase was washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified by MDAP (modifier: formic acid). The appropriate fractions were collected and concentrated in vacuo. The residue obtained was dissolved in water and the aqueous layer was basified with K2CO3 then extracted with DCM (4×10 mL). The combined organic phases were dried over MgSO4 and concentrated in vacuo to give 1-methylethyl[(cis)-1-acetyl-6-(4-{[(2-hydroxyethyl)amino]methyl}-1H-imidazol-1-yl)-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (13 mg, 0.030 mmol, 12%) as a colourless foam.

Provenance & Evidence