Ozone → HCID 19097394, compound

Temperature

-78 °C

2,3,4-trimethyl-3-(3-methyl-2-buten-1-yl)-1-(phenylmethyl)piperidine hydrochloride (24.7 g, 76.7 mmol) was dissolved in ethanol (500 mL) and cooled to -78° C. ozone was bubbled into the reaction mixture until the solution turned blue and the mixture was purged with oxygen, then nitrogen until the solution turned colorless. Sodium borohydride (14.5 g, 383 mmol) was added to the reaction mixture while maintaining the temperature at -78° C. and the solution was stirred at -78° C. for 1 hour. The mixture was slowly warmed to room temperature over a period of 2 hours, 6 H HCl was added to acidify the solution and the solvent was removed in vacuo. The white residue was taken up in water, washed with ether (3×100 mL), basified with aqueous NAOH and extracted with methylene chloride (3×200 mL) The organic layer was dried over Na2SO4 and the solvent was removed in vacuo. The residue was taken up in ether (500 mL), dried over anhydrous MgSO4 and the solvent was removed in vacuo to afford 19.1 g (95%) of 2,3,4-trimethyl-1-(phenylmethyl)-3-piperidineethanol.

1. customwas bubbled into the reaction mixture until the solution
2. customthe mixture was purged with oxygen
3. temperatureThe mixture was slowly warmed to room temperature over a period of 2 hours
4. addition6 H HCl was added
5. customthe solvent was removed in vacuo
6. washwashed with ether (3×100 mL)
7. extractionextracted with methylene chloride (3×200 mL) The organic layer
8. dry with materialwas dried over Na2SO4
9. customthe solvent was removed in vacuo
10. dry with materialdried over anhydrous MgSO4
11. customthe solvent was removed in vacuo

ORD record

ord-ae5a1b64b0bc42048d1e383c65a42379

Source dataset

uspto-grants-1994_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05290789