2-Methylimidazole → HCID 52934335, compound

Participants

Reaction Steps

A mixture of 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 52) (500 mg, 1.2 mmol), 2-methylimidazole (99 mg, 1.2 mmol) and copper(I) oxide (10 mg, 0.126 mmol) in methanol (10 mL) was stirred in air at room temperature for 24 h. A further portion of copper(I) oxide (10 mg, 0.126 mmol) was added and stirring was continued for 48 h. The reaction mixture was then filtered through celite and most of the solvent were removed in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 0 to 5% MeOH in DCM) gave 1-methylethyl[(2S,4R)-1-acetyl-2-methyl-6-(2-methyl-1H-imidazol-1-yl)-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (167 mg, 0.451 mmol, 37%) as a colourless foam.

Provenance & Evidence