Nandrolone phenylpropionate synthesis
- Product Name:Nandrolone phenylpropionate
- CAS Number:62-90-8
- Molecular formula:C27H34O3
- Molecular Weight:406.57
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) δ 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
Yield:62-90-8 74%
Reaction Conditions:
with bis(1-butyl-3-methylimidazolium) tungstate in 1,4-dioxane at 120; for 2.5 h;
Steps:
6
In a 100 ml reaction flask, 0.397 g (3 mmol) of cinnamaldehyde, 0.411 g (1.5 mmol) of Nandrolone, 0.158 g (0.3 mmol) of [Bmim] 2 [WO4] catalyst, and 10 ml of 1,4-dioxane were added and heated. After heating to 120 ° C, the reaction was carried out for 2.5 h. After the reaction was completed, it was cooled to room temperature, extracted with 30 ml of water and 20 ml of ethyl acetate, and the phases were allowed to stand, and the organic phase was concentrated to obtain the target. The product, a yield of 74%.
References:
CN109678718,2019,A Location in patent:Paragraph 0035
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