ChemicalBook CAS DataBase List Misoprostol

Misoprostol synthesis

9synthesis methods

Product Name:Misoprostol
CAS Number:59122-46-2
Molecular formula:C22H38O5
Molecular Weight:382.54

synthesis of Misoprostol
To a 1000 ml dried flask under a nitrogen atmosphere was added 74.6 g of(E)-trimethyl-[[1-methyl-1-[3-(tributylstannyl)-2-propenyl]pentyl]oxy]silane,125 ml anhydrous THF and 24.2 g of copper (I) iodide. The mixture wasstirred at room temperature for 30 minutes and then it was cooled to -25 to -30°C. 98.8 ml of methyllithium (2.86 M) in DEM was added dropwise and theresultant solution was stirred at -15°C for 2 hours. Then the reaction mixturewas cooled to -78°C and 25 g of methyl-5-oxo-3-[(triethylsilyl)oxy]-1-cyclopentene-1-heptanoate in 100 ml of THF was added rapidly. After stirringthe mixture for 5 min at -78°C, it was quenched into a mixture of 750 ml ofaqueous ammonium chloride solution and 200 ml of ammonium hydroxide.The resulting mixture was warmed to room temperature and stirred until adeep blue aqueous layer was obtained. Ethyl acetate (250 ml) was used forextraction. Then the combined organic layers were washed with brine andsubsequently dried over magnesium sulfate. After a filtration andconcentration under reduced pressure, an oil (105 g) was obtained. This oilcontaining the protected prostaglandin was subjected to acidic deprotection(cat. PPTS, acetone and water) and purification (chromatography on silica gel)to provide 15.8 g (60%) of misoprostol was identical.

14273-90-6
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59122-46-2
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$17.00/1mg

Yield:-

Steps:

Multi-step reaction with 6 steps
1: 51 percent / sodium nitrite, phloroglucinol / dimethylsulfoxide / 20 h / Ambient temperature
2: 1) 3N sodium hydroxide; 3) acetic acid / 1) H₂O, 0 deg C, 3 h; 2) H₂O, 0 deg C, 5 h; 3) H₂O, room temp., 20 h
3: 79 percent / mesyl chloride, triethylamine / CH₂Cl₂ / 1 h / 0 °C
4: 1) t-butyllithium; 2) copper(I)iodide, tributylphosphine
5: 42 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 0.17 h / 110 °C
6: 88 percent / hydrogen fluoride-pyridine / acetonitrile / 2 h / Ambient temperature

References:

Tanaka, Toshio;Hazato, Atsuo;Bannai, Kiyoshi;Okamura, Noriaki;Sugiura, Satoshi;et al. [Tetrahedron,1987,vol. 43,# 5,p. 813 - 824]