Hydrochloric Acid → HCID 11619202, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-6-phenylazocan-2-one (18 mg, step H) in THF (0.10 mL) at room temperature was added borane-THF complex (1.50 M solution in THF, 0.10 mL) and the resulting solution was heated at 65° C. in a sealed vial for 3 h. The solution was cooled to room temperature, and methanol (0.10 mL) was added slowly followed by 1N hydrochloric acid (0.10 mL), and the reaction mixture was heated at 65° C. for 2 h. The solvents were removed in vacuo, dichloromethane and 1N sodium hydroxide were added, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo to give the title compound as an oil. 1H NMR (400 MHz, CDCl3) δ 1.58 (5H, m), 2.09 (3H, m), 2.30 (1H, m), 2.94 (4H, m), 3.44 (1H, d, J=8.8 Hz), 3.47 (1H, d, J=8.8 Hz), 4.42 (2H, s), 7.21 (1H, m), 7.37 (4H, m), 7.55 (2H, s), and 7.73 (1H, s). HPLC retention time (1.88 min, column: 4.6×50 mm XTERRA C18 S5, flow rate: 5 mL/min, gradient: 0-100% MeOH/H2O 0.1% TFA over 2 min). MS: 446 (MH+).

Provenance & Evidence