Hydrochloric Acid → HCID 15454080, compound

Participants

Reaction Steps

Following general procedure D and using 5-bromo-3,3-dimethyl-7-ethyl-2,3-dihydro-benzofuran (Compound 9, 1.2 g, 4.72 mmol obtained substantially in accordance with J Med. Chem. 1998, 41, 1124-1137), benzophenone imine (0.94 g, 5.2 mmol), sodium-tert-butoxide (0.63 g, 6.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.020 g, 0.021 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.040 g, 0.064 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 (0.7 g, 78%). 1H NMR (300 MHz, CDCl3): δ 6.37 (d, 1H, J=2.3 Hz), 6.35 (d, 1H, J=2.3 Hz), 4.17 (s, 2H), 3.15 (br s, 2H), 2.54 (q, 2H, J=7.6 Hz), 1.30 (s, 6H), 1.20 (t, 3H, J=7.6 Hz).

Provenance & Evidence