Allyl bromide → 1-tert-Butyl 4-ethyl 4-(prop-2-en-1-yl)piperidine-1,4-dicarboxylate

A solution of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (5 g, 19.37 mmol) in THF (50 mL) was cooled to −78° C. followed by drop wise addition of LDA (1.80 M in THF, 21.67 mL, 38.74 mmol) solution and was stirred at the same temperature for 45 min followed by addition of allyl bromide (5 mL, 58.14 mmol) at −78° C. The temperature of the reaction was slowly raised to rt and left to stir for 5-6 h. The reaction was then cooled to 0° C. and quenched by drop wise addition of saturated NH4Cl solution (50 mL), extracted with EtOAc (3×100 mL) and the combined organics washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 1% EtOAc:hexane to obtain the product as an orange viscous liquid (5 g, 87% yield). MS: 298.19 [M+H]+.

1. waitleft
2. stirringto stir for 5-6 h
3. temperatureThe reaction was then cooled to 0° C.
4. customquenched by drop wise addition of saturated NH4Cl solution (50 mL)
5. extractionextracted with EtOAc (3×100 mL)
6. washthe combined organics washed with brine
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe crude residue was purified over 100-200 M silica-gel

ORD record

ord-cb51b33550b74ba6a0ed6340c453f3a6

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181234B2