ChemicalBook CAS DataBase List Treprostinil Ethyl Ester

Treprostinil Ethyl Ester synthesis

14synthesis methods

Product Name:Treprostinil Ethyl Ester
CAS Number:1355990-07-6
Molecular formula:C25H38O5
Molecular Weight:418.57

105-36-2 Synthesis

105-36-2
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(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-Hexahydro-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]indene-2,5-diol

101692-02-8
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1355990-07-6
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Yield:1355990-07-6 96%

Reaction Conditions:

with potassium carbonate;potassium iodide in acetone; for 16 h;Inert atmosphere;Reflux;

Steps:

27 Example 27: ethyl 2-(((l/f,2/f,3a5,9a5)-2-hydroxy-l-((5)-3-hydroxyoctyl)- 2,3,3a,4,9,9a-hexahydro-lH-cyclopenta[b]naphthalen-5-yl)oxy)acetate(25a)

Example 27: ethyl 2-(((l/f,2/f,3a5,9a5)-2-hydroxy-l-((5)-3-hydroxyoctyl)- 2,3,3a,4,9,9a-hexahydro-lH-cyclopenta[b]naphthalen-5-yl)oxy)acetate(25a) [0432] Ethyl bromoacetate was added drop-wise to a slurry of benzindene triol 24a (500 mg, 1.504 mmol, 1.0 equiv), anhydrous potassium carbonate (312 mg, 2.26 mmol, 1.5 equiv) and anhydrous potassium iodide (25 mg, 0.15 mmol, 0.1 equiv) in acetone (20 mL) and the reaction was heated to reflux while stirring, under nitrogen for 16 hours. The reaction was then cooled to room temperature, diluted with heptane (10 mL) and filtered through celite. The celite was rinsed with ethyl acetate (3 x 30 mL) and the filtrate was concentrated to give a pale oil. Chromatography (10% to 80% ethyl acetate/heptane gradient) afforded 610 mg (96%) of the title compound as a colorless oil. Data for 25a: R_f = 0.15 (50% EtOAc / heptane); *H NMR *H NMR (400 MHz, CDC1₃) δ 7.07 (t, 7=7.87 Hz, 1H), 6.81 (d, 7=7.32 Hz, 1H), 6.64 (d, 7=7.69 Hz, 1H), 4.62 (s, 2H), 4.27 (q, 7=7.32 Hz, 2H), 3.76 (dt, 7=6.04, 9.61 Hz, 1H), 3.55-3.70 (m, 7=4.40 Hz, 1H), 2.89 (dd, 7=5.86, 14.65 Hz, 1H), 2.76 (dd, 7=6.23, 14.28 Hz, 1H), 2.56 (dd, 7=6.59, 15.01 Hz, 1H), 2.46 (dd, 7=6.59, 14.28 Hz, 1H), 2.11-2.34 (m, 4H), 1.89 (tt, 7=6.50, 9.98 Hz, 1H), 1.24-1.75 (m, 16H), 1.12-1.23 (m, 1H), 0.84-0.99 (m, 3H); MS (ESI+) m/z 419.3 (M+H⁺).

References:

WO2014/89385,2014,A2 Location in patent:Paragraph 0431-0432

64-17-5 Synthesis