Ammonium Chloride → HCID 11047710, compound

Participants

Reaction Steps

A solution of 341 mg (0.850 mmol) of 71, 129 mg (3.40 mmol) of NaBH4 in THF (9 mL) with 37 drops of H2O was stirred at rt for 3 h, poured into saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (3×, 50 mL). Combined organic extracts were washed with 10% Na2S2O5 (30 mL), H2O (30 mL), dried over Na2SO4 and concentrated in vacuo giving a yellow oil. Purification by flash chromatography on a 3×21 cm column of silica gel using 2:1 hexanes/EtOAc as eluent gave 311 mg (91%) of 72. Data for 72: TLC, T-1, Rf 0.37; 1H NMR (500 MHz, CDCl3) δ 0.83 (s, 3H, H-18), 1.02 (t, 1H, J=10.3 Hz, H-14), 3.70 (t, 1H, J=9.2 Hz, H-17α), 5.01–5.06 (m, 2H, ═CH2), 5.04 (s, 2H, benzylic-H), 5.78–5.86 (m, 1H, —CH═), 6.72 (d, 1H, J=2.7 Hz, H-4), 6.79 (dd, 1H, J=8.6, 2.7 Hz, H-2), 7.22 (d, 1H, J=8.6 Hz, H-1), 7.31–7.44 (m, 5H, Ar—H).

Provenance & Evidence