Hydrochloric Acid → HCID 23021118, compound

To a solution of benzyl cyclohexanecarboxylate (1.44 g) in tetrahydrofuran (40 mL) was added a 1M solution of lithium hexamethyldisilazane in tetrahydrofuran (9.9 mL) under ice cooling. The solution was stirred at room temperature for 1 hour under ice cooling, to which hexamethylphosporamide (2.3 mL) was added. The solution was then stirred for additional 10 minutes. To the solution was added allyl bromide (1.4 mL). The solution was stirred under ice cooling for 1 hour, to which allyl bromide (1.4 mL) was further added. The solution was stirred at room temperature for 18 hours. Water and 3N hydrochloric acid were added to the solution, and it was extracted with diethyl ether. The organic layer was washed in turn with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The solution was dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=99:1) to give the title compound (550 mg). This product was subjected to the subsequent step without further purification.

1. additionwas added
2. stirringThe solution was then stirred for additional 10 minutes
3. additionwas further added
4. stirringThe solution was stirred at room temperature for 18 hours
5. extractionwas extracted with diethyl ether
6. washThe organic layer was washed in turn with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
7. dry with materialThe solution was dried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=99:1)

ORD record

ord-528aab83aa3942a8b446cd62cbdab7fa

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07375115B2