2,3-Dibromopropene → 1-Tert-butyl 4-ethyl 4-(2-bromoallyl)piperidine-1,4-dicarboxylate

Temperature

-78 °C

Lithium diisopropylamide (29.1 mL, 58.3 mmol) was added dropwise at −78° C. To a solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (9.56 mL, 38.9 mmol) in THF (200 mL), and stirred at this temperature for 50 min. 2,3-Dibromoprop-1-ene (5.47 mL, 56.0 mmol) in THF (10 mL) was added to the reaction mixture slowly and the resulting mixture was stirred for 1.5 hr at −78° C. The reaction mixture was quenched with NH4Cl solution (15 mL) and was allowed to warm to room temperature and the aqueous layer was extracted with EtOAc (30 mL×3). The combined organics were washed with brine (30 mL), dried over MgSO4 and concentrated to get the crude product which was purified by silica gel column chromatography (RediSep 220 g Gold column) using (0-30) % EtOAc/Hexanes as mobile phase to give the title compound.

1. customThe reaction mixture was quenched with NH4Cl solution (15 mL)
2. temperatureto warm to room temperature
3. extractionthe aqueous layer was extracted with EtOAc (30 mL×3)
4. washThe combined organics were washed with brine (30 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. customto get the crude product which
8. customwas purified by silica gel column chromatography (RediSep 220 g Gold column)

ORD record

ord-fa7c101b443f452c8dd015b4dbc6757d

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952166B2