Compounds and methods involving sterols
A technology for compounds and oxysterols, applied in the field of compounds and methods involving sterols, capable of solving problems such as reduced safety, low yield, and adverse environmental effects
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Embodiment 1
[0175] Prepared from pregnenolone acetate
[0176] Under vigorous magnetic stirring and ice-bath cooling, 8.25 mL of n-hexylmagnesium chloride (2M, 16.5 mmol) in THF was added to the solution of pregnenolone acetate in THF. Pregnenolone acetate solution contained 1.79 g of compound 1, pregnenolone acetate (5 mmol) in 4.5 mL THF. The addition was carried out over 2 minutes. After the addition was complete, the mixture was stirred at room temperature for 3.5 hours, at which time the mixture became a gel. Then with saturated NH 4 A mixture of aqueous Cl and MTBE (methyl tert-butyl ether) digested the gel. The organic layer was separated, washed three times with water and evaporated. The residue was separated by column chromatography on silica gel using EtOAc (ethyl acetate) / petroleum ether mixture (ratio 70 / 30) to afford compound 2, diol, as a white solid. 1.29 g (3.21 mmol) of solid diol were extracted in an isolated yield of 64%. The reaction is shown in A below:
[0177...
Embodiment 2
[0181] Prepared from pregnenolone
[0182] Except for Example 1, Compound 2 of Reaction Scheme A above can be prepared from pregnenolone in B below using the same procedure as used to convert Compound 1 to Compound 2. In this method, 10 g of pregnenolone was converted to 7.05 g of compound 2, representing a 55% yield.
[0183]
[0184] Reaction Scheme B
[0185] 2500 mL of n-hexylmagnesium chloride (2M, 5 mol) was added into the reactor, and the solution was cooled to -5°C. A solution of pregnenolone acetate in THF was added to the reactor at a rate that kept the internal reaction temperature below 1 °C. The pregnenolone solution contained 500 g of pregnenolone (1.4 moles) in 8 liters of THF. After the addition was complete, the mixture was maintained at 0°C for 1 hour and then allowed to warm to room temperature overnight. The reaction mixture had turned into a solid gel-like substance. An additional 2 liters of THF was added, followed by 10 ml of glacial acetic acid....
Embodiment 3
[0188] The crude hexanediol product (800 grams) was dissolved in 8 liters of THF, charged to the reactor, and cooled to -5°C. The borane-THF complex (IM, 6.3 mol, 4.5 equiv) in 6300 mL THF was added at a rate to maintain the internal reaction temperature below 1 °C. Once the addition was complete, the reaction mixture was stirred at 0°C for 1.5 hours, then allowed to warm to room temperature overnight. The reaction is shown below.
[0189]
[0190] The reaction mixture was quenched by adding a mixture of 10% sodium hydroxide (4750 mL) and 30% hydrogen peroxide (1375 mL). Quenching is extremely exothermic and takes several hours to complete. The internal temperature is kept below 10°C. After the addition of the quench volume was complete, the mixture was kept cool for 1.5 hours and then allowed to warm to room temperature overnight. Then 8 liters of dichloromethane were added. The organic layer was separated and washed with 7 L of fresh water, and concentrated under red...
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