Anabolic steroid; androgen.
Nandrolone phenylpropionate, an anabolic steroid, was
introduced in 1959. In 1982, low dosage preparations were prohibited in
Bangladesh due to inadmissible promotion of products containing anabolic
steroids for malnourished children. Higher dosage preparations of nandrolone
phenylpropionate remain available in many countries, including Bangladesh, for
several highly specific but limited indications that apply to patients with chronic
debilitating and emaciating diseases, particularly associated with neoplasia and
some types of aplastic anaemia.
Nandrolone phenylpropionate is prepared by reacting anhydrous MeCN with a mixture of 3-phenylpropanoic acid, aryneprecursor, nandrolone CsF, K2CO3, and 18-crown-6 in 70 ?? in an oil bath.
Add anhydrous MeCN (0.5 mL) to a mixture of 3-phenylpropanoic acid (30.0 mg, 0.2 mmol, 1.0 equiv), aryneprecursor (119.2 mg, 0.4 mmol, 2.0 equiv), nandrolone (82.3 mg, 0.3 mmol, 1.5 equiv), CsF (182.3 mg, 1.2 mmol, 6.0 equiv), K2CO3 (82.9 mg, 0.6 mmol, 3.0 equiv), and 18-crown-6 (158.6 mg, 0.6 mmol, 3.0 equiv). Warm the mixture to 70 ?? in an oil bath and stir at this temperature for8 hours. Remove all the volatiles directly on rotary evaporator. Purify by flash column chromatography with pet ether:EtOAc = 20:1. 1H NMR (400 MHz, CDCl3) |? 7.31-7.26(m,2H), 7.23-7.17(m,3H), 5.83 (s, lH), 4.65-4.58(m, lH), 2.95(t, J= 8.0 Hz,2H), 2.64(t, J= 8.0 Hz,2H), 2.51-2.36(m, 2H), 2.31-2.04(m, 5H), 1.86-1.79(m, 2H), 1.72-1.61 (m, 2H), 1.57-1.00(m, 8H),0.90-0.81(m, 1H), 0.79 (s, 3H)ppm.
Fig The synthetic method 1 of Nandrolone phenylpropionate