Hydrochloric Acid → HCID 57565074, compound

Temperature

65 °C

To a solution of 5-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-5-phenylazocan-2-one (16 mg) in THF (0.10 mL) at room temperature was added borane-THF complex (1.50 M solution in THF, 93 μL) 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 1.57 (4H, m), 1.87 (1H, broad, s), 2.09 (4H, m), 2.72 (2H, m), 2.88 (2H, m), 3.43 (2H, s), 4.41 (2H, s), 7.21 (1H, m), 7.39 (4H, m), 7.54 (2H, s), and 7.21 (1H, s). HPLC retention time (1.87 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+).

1. temperatureThe solution was cooled to room temperature
2. temperaturethe reaction mixture was heated at 65° C. for 2 h
3. customThe solvents were removed in vacuo, dichloromethane and 1N sodium hydroxide
4. additionwere added
5. extractionthe aqueous layer was extracted with dichloromethane
6. washThe combined organic layers were washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. customThe filtrate was evaporated in vacuo

ORD record

ord-3e02691db3054994841abf9327aaf3b5

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07494986B2