Water → (4-{4-(2-Azidoacetyl)-phenyl]-cyclohexyl}-acetic acid ethyl ester

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Reaction Steps

To a solution of {4-[4-(2-bromoacetyl)-phenyl]-cyclohexyl}-acetic acid ethyl ester (166 mg, 0.451 mmol) in acetone/water (4:1, v/v, 5 mL) is added NaN3 (44 mg, 0.676 mmol) and the mixture is stirred at ambient temperature for 2 h. Water (10 mL) is added and EtOAc is used to extract. The organic phase is dried with MgSO4, concentrated, and dried under high vacuum to give the title compound (154 mg): 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.05-1.16 (m, 2H) 1.20 (t, J=7.07 Hz, 3H) 1.40-1.49 (m, 2H) 1.84 (d, J=10.11 Hz, 4H) 1.76-1.87 (m, 1H) 2.17 (d, J=6.82 Hz, 2H) 2.48 (tt, J=112.25, 3.03 Hz, 1H) 4.08 (q, J=7.16 Hz, 2H) 4.45 (s, 2H) 7.25 (d, J=8.34 Hz, 2H) 7.76 (d, J=8.34 Hz, 2H).

Provenance & Evidence