Hydrochloric Acid → 5-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

Participants

Reaction Steps

Following general procedure D and using 5-bromo-7-t-butyl-3,3-dimethyl-2,3-dihydro-benzofuran (Compound 10, see J. Med. Chem. 1998, 41, 1124-1137; 2.0 g, 5.5 mmol), benzophenone imine (1.2 g, 6.64 mmol), sodium-tert-butoxide (0.74 g, 7.75 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.025 g, 0.026 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.050 g, 0.078 mmol) in 10 mL of anhydrous toluene, followed by hydrolysis of the intermediary imine with 2M hydrochloric acid in tetrahydrofuran, the title compound was obtained as an oil (0.95 g, 72%). 1H NMR (300 MHz, CDCl3): δ 6.49 (d, 1H, J=2.4 Hz), 6.39 (d, 1H, J=2.4 Hz), 4.17 (s, 2H), 3.38 (br s, 2H), 1.37 (s, 9H), 1.32 (s, 6H).

Provenance & Evidence