Hydrochloric Acid → HCID 67205065, compound

Participants

Reaction Steps

A solution of 1,1-dimethylethyl((2S,4R)-1-acetyl-2-methyl-6-{[tris(1-methylethyl)silyl]ethynyl}-1,2,3,4-tetrahydro-4-quinolinyl)carbamate (for a preparation see Intermediate 107) (1.96 g, 4.04 mmol) in 1,4-dioxane (10 mL) at room temperature was treated with HCl (4N in dioxane, 20 mL, 80 mmol) and the resulting mixture was stirred at this temperature for 7 h then the solvent was removed in vacuo. The residue was triturated with Et2O then filtered off and dried under house vacuum to give (2S,4R)-1-acetyl-2-methyl-6-{[tris(1-methylethyl)silyl]ethynyl}-1,2,3,4-tetrahydro-4-quinolinamine hydrochloride (1.28 g, 3.04 mmol, 75% yield) as a white solid. The mother liquors were concentrated in vacuo to give (2S,4R)-1-acetyl-2-methyl-6-{[tris(1-methylethyl)silyl]ethynyl}-1,2,3,4-tetrahydro-4-quinolinamine hydrochloride (396 mg, 0.940 mmol, 23.26% yield) as a very pale yellow foam.

Provenance & Evidence