Acetic Acid → 1-tert-butyl 3-methyl (3R,5S)-5-[(2-methylpropyl)amino]piperidine-1,3-dicarboxylate

1-tert-Butyl 3-methyl (3R,5S)-5-aminopiperidine-1,3-dicarboxylate (1.83 g), isobutyraldehyde (0.78 ml) and acetic acid (0.49 ml) were dissolved in methanol (50 ml), and the mixture was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (3.80 g) was added to the reaction mixture, and the mixture was stirred at room temperature for 7 hr. The reaction mixture was concentrated under reduced pressure, the concentrated solution was basified with aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography. The fraction eluted with ethyl acetate-hexane (1:1) to ethyl acetate 100% to ethyl acetate-methanol (9:1) was concentrated under reduced pressure to give the object compound (1.42 g) as an oil.

1. stirringthe mixture was stirred at room temperature for 7 hr
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with water and saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. customthe residue was purified by silica gel column chromatography
8. washThe fraction eluted with ethyl acetate-hexane (1:1) to ethyl acetate 100% to ethyl acetate-methanol (9:1)
9. concentrationwas concentrated under reduced pressure

ORD record

ord-14178e651fd34769966a1b564899d03b

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329691B2