1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59846403, compound

Participants

Reaction Steps

DBU (27.1 mL, 180.5 mmol, 3 equiv.) was added to a solution of (S)-7-Fluoro-1,2,3,4-tetrahydronaphthalen-1-ol (10 g, 60.2 mmol, 1 equiv.) in toluene (300 mL). The resulted dark red solution was cooled in ice bath. Diphenylphosphoryl azide (38.6 mL, 180.6 mmol, 3 equiv) was added drop-wise within 30 min. The reaction solution was slowly brought to RT and stirred overnight. TLC was checked and showed no more SM. The reaction was diluted with methylene chloride (200 mL). The methylene chloride layer was washed with saturated NaHCO3, brine, water, saturated NH4Cl, and brine. The organic layer was separated and dried (Na2SO4), evaporated under reduced pressure to give a dark-red syrup which was purified on ISCO (80 g column, 0-2% EtOAc-hexane) to give a colorless oil product (7.9 g, 70%). 1H NMR (400 MHz, CDCl3) δ 7.07-7.11 (m, 1H), 7.02 (dd, 1H), 6.91-6.96 (m, 1H), 4.51 (t, 1H), 2.69-2.86 (m, 2H), 1.76-2.05 (m, 4H).

Provenance & Evidence