Allyl bromide → HCID 118390116, compound

To a solution of tert-butyl 2-oxopiperidine-1-carboxylate (8.22 g, 41.3 mmol) in anhydrous THF (80 mL) was added LiHMDS (1.0 M in THF, 103 mL, 103 mmol) dropwise under nitrogen atmosphere at −78° C. and the reaction mixture was stirred for 20 min at the same temperature and then 3-bromoprop-1-ene (10.7 mL, 124 mmol) was added to. The resulting mixture was stirred for 15 min at −78° C. and warmed to rt, quenched with water (15 mL), and concentrated in vacuo. The residue was diluted with water (30 mL) and extracted with EtOAc (50 mL×3). The combined organic phases were washed with brine (50 mL), then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/50) to give the title compound as yellow oil (3.95 g, 35%).

1. stirringThe resulting mixture was stirred for 15 min at −78° C.
2. customquenched with water (15 mL)
3. concentrationconcentrated in vacuo
4. additionThe residue was diluted with water (30 mL)
5. extractionextracted with EtOAc (50 mL×3)
6. washThe combined organic phases were washed with brine (50 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/50)

ORD record

ord-2b533fc8e5b24d9b9ce15e6bd0b54a24

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403801B2