Sodium Azide → (1R,2S)-2-azidocyclohexyl 4-bromophenyl ether

Temperature

120 °C

To a solution of (1R,2R)-2-(4-bromophenoxy)cyclohexyl methanesulfonate (3.55 g, 10.2 mmol) in dimethylformamide (21.8 mL) and water (2.43 mL) was added sodium azide (95%, 2.09 mg, 30.5 mmol) and the reaction was heated at 120° C. for 23 hours. The reaction was cooled to room temperature, diluted with water (400 mL) and extracted with ethyl acetate (4×400 mL). The combined organic layers were washed with aqueous lithium chloride solution (1N, 400 mL), washed with water (400 mL), and dried over magnesium sulfate. Filtration and removal of solvents in vacuo afforded (1R,2S)-2-azidocyclohexyl 4-bromophenyl ether as an orange oil, which was used in the next step without additional purification. Yield: 2.85 g, 9.62 mmol, 94%. 1H NMR (400 MHz, CDCl3) δ 1.36-1.48 (m, 2H), 1.62-1.76 (m, 4H), 1.96-2.07 (m, 2H), 3.63 (m, 1H), 4.43 (m, 1H), 6.85 (d, J=9.0 Hz, 2H), 7.39 (d, J=8.9 Hz, 2H).

1. temperatureThe reaction was cooled to room temperature
2. extractionextracted with ethyl acetate (4×400 mL)
3. washThe combined organic layers were washed with aqueous lithium chloride solution (1N, 400 mL)
4. washwashed with water (400 mL)
5. dry with materialdried over magnesium sulfate
6. filtrationFiltration and removal of solvents in vacuo

ORD record

ord-38a13f8ca70d4797b32fe138ff390e08

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08686043B2