Water → (2beta,3alpha)-3-Hydroxy-2-(piperazin-1-yl)androstan-17-one

Participants

Reaction Conditions

Reaction Steps

To compound 22 (202 mg, 0.70 mmol) was added water (1 mL) and piperazine (3.5 g, 41 mmol). The solution was subsequently heated at 150° C. over a period of 24 h. The resulting mixture was diluted with dichloromethane (50 mL) and washed with water, dried with Na2SO4, filtered and evaporated under reduced pressure. The crude compound was purified by flash chromatography (DCM/MeOH: 9:1 containing 0.5% of TEA) to yield compound 23 (169 mg, 65%). 1H NMR (CDCl3) δ: 0.87 (s, 18-CH3 and 19-CH3), 0.73-2.17 (residual CH and CH2), 2.45, 2.64 and 2.91 (3m, 4×CH2N and 2α-CH), 3.85 (m, 3β-CH).

Provenance & Evidence