反应详情

(R)-1-Boc-piperidine-3-carboxylic acid phenyl amide 26 (5.26 g, 17.28 mmol) in 20 mL of dry THF was added slowly to 34.5 mL of 1.0 M borane in THF while stirring in an ice bath. The mixture was refluxed for 2 hours, then cooled in an ice bath, and quenched with 20 mL of aqueous HCl (10%), then treated with NaOH (10%) to pH ˜10. The mixture was extracted with ethyl acetate (3×100 mL). The extracts were combined and washed with brine (2×50 mL), and dried over anhydrous sodium sulfate. After the solvent was removed, the remaining oily residue was passed through a short column (silica gel, ethyl acetate) to afford (R)-N-(1-Boc-piperidin-3-ylmethyl)-aniline 28 as a colorless oil (4.59 g, 91%).

1. temperatureThe mixture was refluxed for 2 hours
2. temperaturecooled in an ice bath
3. customquenched with 20 mL of aqueous HCl (10%)
4. additiontreated with NaOH (10%) to pH ˜10
5. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
6. washwashed with brine (2×50 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. customAfter the solvent was removed