Methanol → HCID 45272335, compound

Participants

Reaction Steps

To a stirring cold solution of compound 51 (220 mg, 0.492 mmol) in dry THF was added BH3.THF (211 mg, 2.46 mmol) and the reaction mixture was refluxed overnight. After cooling the reaction mixture to room temperature, 1 ml of methanol was added and the solvent was evaporated. The residue was dissolved in 15 ml of conc. HBr and refluxed for 1 h. The solvent was evaporated and the crude product was dissolved in dichloromethane (50 ml). The organic layer was washed with saturated NaHCO3 (30 ml) and dried over Na2SO4. The solvent was evaporated and the crude product was purified by flash column chromatography over silica gel using ethyl acetate/MeOH/Et3N (95:5:0.2) to afford 52 (20 mg). 1H NMR (400 MHz, CD3OD) δ 0.95 (t, 3H, J=7.6 Hz), 1.53-1.67 (m, 3H), 2.08 (d, 1H, J=9.6 Hz), 2.60-2.88 (m, 14H), 3.10-3.13 (m, 5H), 6.35 (d, 1H, J=2.8 Hz), 6.52-6.55 (m, 2H), 6.87 (d, 1H, J=8.8 Hz), 6.91-6.94 (dd, 1H, J=8.8 Hz and 2.4 Hz), 7.16-7.17 (m, 2H), 7.29 (d, 1H, J=8.8 Hz). Free base converted into oxalate salt, m.p. 179-183° C.

Provenance & Evidence