1-Butanol → HCID 67195717, compound

Participants

Reaction Conditions

Reaction Steps

1-Methylethyl[(2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation, see Example 4) (2.4 g, 6.50 mmol), N,N-dimethyl-4-pyridinamine (1.588 g, 13.00 mmol), trans-di-mu(m)-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II) (Hermann's catalyst) (0.305 g, 0.325 mmol), 1-butanol (7.23 g, 97 mmol), molybdenum hexacarbonyl (0.858 g, 3.25 mmol), DIPEA (1.680 g, 13.00 mmol) were combined with 1,4-dioxane (2 mL) in 2 sealed 20 mL vials and the mixture was stirred at 180° C. for 30 min under microwave irradiation, then cooled to room temperature. The microwave seals were distinctly raised on completion of the reaction and the pressure was released by use of a 20 mL syringe and needle. The vials were opened and the black reaction mixtures were combined in a 250 mL conical flask, diluted with EtOAc (40 mL) and treated with water. The layers were separated and the organic phase was dried over MgSO4 then concentrated in vacuo. Purification of the residue using SP4 on a 50 G silica cartridge (gradient: 0-100% AcOEt in Hexanes) gave butyl (2S,4R)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinecarboxylate (1.822 g, 4.67 mmol, 71.8% yield)

Provenance & Evidence