Water → (1S,2R)-2-(4-bromophenoxy)cyclohexanamine

A solution of (1R,2S)-2-azidocyclohexyl 4-bromophenyl ether from the previous step (2.85 g, 9.62 mmol) in tetrahydrofuran (59 mL) and water (4.6 mL) was treated with polymer-supported triphenylphosphine (3 mmol/g, 7.87 g, 23.6 mmol). The reaction was stirred for 18 hours, then filtered through Celite®. The filter pad was rinsed with tetrahydrofuran (250 mL), then with ethyl acetate (400 mL), and the combined filtrates were concentrated in vacuo, and azeotroped with ethanol. The residue was purified by chromatography on silica gel (Gradient: 0% to 10% methanol in dichloromethane) to afford (1S,2R)-2-(4-bromophenoxy)cyclohexanamine as a yellow oil. Yield: 1.82 g, 6.74 mmol, 70%. 1H NMR (400 MHz, CDCl3) δ 1.33-1.55 (m, 4H), 1.66-1.75 (m, 3H), 2.00 (m, 1H), 2.07 (br s, 2H), 2.97 (m, 1H), 4.39 (m, 1H), 6.85 (d, J=9.0 Hz, 2H), 7.36 (d, J=9.0 Hz, 2H).

1. filtrationfiltered through Celite®
2. washThe filter pad was rinsed with tetrahydrofuran (250 mL)
3. concentrationwith ethyl acetate (400 mL), and the combined filtrates were concentrated in vacuo
4. customazeotroped with ethanol
5. customThe residue was purified by chromatography on silica gel (Gradient: 0% to 10% methanol in dichloromethane)

ORD record

ord-79cfe38da2aa478f8f3559e7ddc9b24d

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08686043B2