1-Hydroxybenzotriazole → Androstan-17-one

Participants

Reaction Steps

To a solution of compound 23 (150 mg, 0.40 mmol) in anhydrous DMF (7 mL) at room temperature under an atmosphere of argon were added carboxylic acid 20 (119 mg, 0.44 mmol), PyBOP (229 mg, 0.44 mmol), HOBt (60 mg, 0.44 mmol), and DIPEA (220 μL, 1.26 mmol). The solution was subsequently stirred overnight at room temperature. The resulting solution was then poured into water and extracted with EtOAc (2×30 mL), washed with brine, dried with MgSO4 and evaporated to dryness. Purification by flash chromatography (Hexanes/Acetone: 1:1) yielded 157 mg (63%) of compound 24. 1H NMR (CDCl3) δ: 0.89 (s, 18-CH3 and 19-CH3), 0.70-2.50 (residual CH and CH2), 3.45-3.90 (broad, NCH2 of proline and 2×CH2NCO), 3.95 (m, 3β-CH), 5.09 (broad, NCHCO of proline), 7.55 (m, 2×CH of naphthalene), 7.61 (m, CH of naphthalene), 7.87 (m, 3×CH of naphthalene), 8.06 (s, CH of naphthalene).

Provenance & Evidence