Hydrochloric Acid → HCID 69427878, compound

Participants

Reaction Steps

3-(3-Aza-bicyclo[3.2.1]oct-8-yl)-phenol as HCl salt (547 mg, 1.93 mmol) was stirred vigorously in 1N NaOH (10 mL), saturated aqueous Na2CO3 solution (20 mL) and CH2Cl2 (30 mL) then charged with benzyl chloroformate (5 mL, 35.0 mmol) slowly via syringe. After stirring overnight, the layers were separated and the product was extracted with CH2Cl2 (1×10 mL), washed with saturated aqueous NaHCO3 solution, dried through a cotton plug and concentrated to a brown liquid. Flash chromatography provided the desired product as a thick clear oil (420 mg, 65%). (TLC 30% EtOAc/hexanes Rf 0.34); 1H NMR (400 MHz, CDCl3) δ 7.33 (m, 5H), 7.11 (t, J=7.9 Hz, 1H), 6.73 (d, J=7.9 Hz, 1H), 6.71 (s, 1H), 6.66 (d, J=7.9 Hz, 1H), 5.14 (s, 2H), 4.05 (dd, J=12.2 Hz, 2.7 Hz, 1H), 3.96 (dd, J=12.2, 2.7 Hz, 1H), 3.09 (m, 2H), 2.85 (s, 1H), 2.50 (br s, 1H), 2.46 (br s, 1H), 1.64 (m, 2H), 1.48 (m, 2H).

Provenance & Evidence