Water → HCID 67771149, compound

Participants

Reaction Steps

(2RS,3SR)-3-(tert-Butyldimethylsilyloxy)methyl-2-diallylaminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (2.17 g, 4.62 mmol) was dissolved in a solvent mixture (60 ml) of tetrahydrofuran--N,N-dimethylformamide (5:1), to which tetra-n-butylammonium chloride (1.0 M tetrahydrofuran solution, 10 ml, 10.0 mmol) was added, followed by stirring at room temperature for 8 hours. The reaction mixture was condensed under reduced pressure, and the resultant residue was separated by silica gel column chromatography (chloroform--methanol =50:1). All the fractions that contain spots in the vicinity of Rf=0.4 were collected, and condensed under reduced pressure. The resultant residue was dissolved in ethanol (100 ml). To the solution, Wilkinson catalyst (140.0 mg, 0.15 mmol), 1,4-diazabicyclo[2,2,2]octane (200.0 mg, 1.78 mmol) and water (10 ml) were added, and the mixture was refluxed with heat for 2 hours. The reaction mixture was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform: saturated ammonia--methanol=50:1). Crude crystals were obtained (500 The crude crystals were dissolved in a solvent mixture of chloroform and methanol (4:1), to which 4N-HCl--dioxane (0.6 ml, 2.40 mmol) was added. The resultant mixture was condensed under reduced pressure, then subjected to azeotropic distillation along with methanol (twice). The residue was recrystallized from methanol--ether. 521.7 mg of the title compound was obtained as pale yellow powdery crystals (38.1%).

Provenance & Evidence