Sodium Iodide → HCID 68185410, compound

Participants

Reaction Steps

To a solution of 1-methylethyl[(2S,4R)-1-acetyl-6-amino-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 112) (1.46 g, 4.78 mmol) in acetone (15 mL) at 60° C. was added potassium carbonate (0.991 g, 7.17 mmol) and the resulting mixture was stirred at this temperature for 15 min. 1-Chloro-2-propanone (0.457 ml, 5.74 mmol) was added as well as sodium iodide (0.860 g, 5.74 mmol) and resulting mixture was stirred at 60° C. for 1 h then cooled to room temperature, filtered through celite and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 10 to 100% AcOEt in Hexanes) gave 1-methylethyl {(2S,4R)-1-acetyl-2-methyl-6-[(2-oxopropyl)amino]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (1.11 g, 3.07 mmol, 64%) as an orange foamy solid.

Provenance & Evidence