ChemicalBook CAS DataBase List 26,27-Dinorergost-5-ene-3β,24-diol

26,27-Dinorergost-5-ene-3β,24-diol synthesis

8synthesis methods

Product Name:26,27-Dinorergost-5-ene-3β,24-diol
CAS Number:35882-85-0
Molecular formula:C26H44O2
Molecular Weight:388.63

3β-Acetoxychola-5-ene-24-oic acid methyl ester

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676-58-4 Synthesis

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Yield:35882-85-0 97%

Reaction Conditions:

in tetrahydrofuran at 0 - 20; for 2.25 h;Inert atmosphere;

Steps:

15 [00373] Preparation of compound BB-2:

[00373] Preparation of compound BB-2: Under nitrogen a solution of BB-1 (1.75 g, 4.06 mmol) in THF (35 mL), prepared as described in Steroids (2006) 71: 18, was cooled to 0°C. Methylmagnesium chloride (22% (w/w) in THF, 19.5 mL, 58.1 mmol) was added dropwise. Stirring at 0°C was continued for 15 minutes and reaction mixture was allowed to warm to room temperature and stirring was continued for two hours. Saturated aqueous NH₄CI (5 mL) was added slowly. Precipitate formed and was dissolved by addition of water (10 mL). EtOAc (50 mL) and brine (20 mL) were added. Layers were separated. Aqueous layer was extracted with EtOAc (2 x 50 mL). Combined organic layers were dried with Na₂S0₄ and solvents were removed in vacuo. Residue was coevaporated with dichloromethane (50 mL). BB-2 (1.54 g, 3.95 mmol, 97%) was obtained as an off-white solid. 1HNMR (400 MHz, CDC1₃): 5(ppm): 5.32 - 5.43 (1H, m), 3.46 - 3.61 (1H, m), 1.20 (3H, s), 1.19 (3H, s), 1.01 (3H, s), 0.93 (3H, d, J = 6.6 Hz), 0.68 (3H, s).

References:

WO2013/36835,2013,A1 Location in patent:Paragraph 00373