Hydrochloric Acid → HCID 70926934, compound

3,4-dihydro-2H-pyran (10.6 mL) was dissolved in methylene chloride (16.2 mL), and to the resultant solution, a 4M hydrogen chloride solution in 1,4-dioxane (31.1 μL) was added, and to the resultant reaction mixture, (1S)-4-bromo-2,3-dihydro-1H-inden-1-ol (10.0 g) that is commercially available or can be obtained by a publicly known method was added, followed by stirring the resultant reaction mixture at room temperature for 3 hours. To the reaction mixture, a saturated sodium hydrogen carbonate aqueous solution (60 mL) was added, followed by extracting the resultant reaction mixture with methylene chloride (60 mL), and the organic phase was washed with a saturated saline (60 mL), followed by drying the organic phase over anhydrous sodium sulfate. From the organic phase, the solvent was distilled off under reduced pressure, followed by purifying the resultant residue by silica gel column chromatography (eluate; n-hexane:ethyl acetate=95:5), and from the resultant, the solvent was distilled off under reduced pressure to obtain the subject compound (15 g). The compound is a mixture of diastereomers.

1. customcan be obtained by a publicly known method
2. additionwas added
3. customreaction mixture at room temperature for 3 hours
4. extractionby extracting the resultant
5. customreaction mixture with methylene chloride (60 mL)
6. washthe organic phase was washed with a saturated saline (60 mL)
7. dry with materialby drying the organic phase over anhydrous sodium sulfate
8. distillationFrom the organic phase, the solvent was distilled off under reduced pressure
9. customby purifying the resultant residue by silica gel column chromatography (eluate; n-hexane:ethyl acetate=95:5)
10. distillationfrom the resultant, the solvent was distilled off under reduced pressure

ORD record

ord-f57eaa32b68446418d89ee0ab53c645d

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08765752B2