Ammonia → HCID 68185409, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see example 4) (2.71 g, 7.34 mmol) and copper(I) oxide (0.247 g, 1.726 mmol) in N,N-dimethylformamide (DMF) (5 mL) was treated with NH3 (35% w/w in water) (5 mL, 258 mmol) and the resulting mixture was stirred at 110° C. for 5 h under microwave irradiation then cooled to room temperature and concentrated in vacuo. The residue was partitioned between water and AcOEt and the layers were separated. The aqueous phase was extracted with AcOEt (2×50 mL) and the combined organic phases were dried over MgSO4 then 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-6-amino-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (1.91 g, 6.25 mmol, 85%) as an orange foamy solid.

Provenance & Evidence