Allyl bromide → 3-(1-Allyl-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid methyl ester

Temperature

-79 °C

0.220 ml of NaHMDS solution (1.0 M in THF, 0.22 mM) was added to 0.5 ml of the THF solution containing 40 mg of 3-(2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionic acid methyl ester (0.218 mM) prepared by the Step 1 in a dropwise manner at −79° C. and stirred at −79° C. for 30 mins. After 0.028 ml of allyl bromide (0.327 mM) was added to the reaction mixture, the mixture was stirred at 0° C. for 3 hrs. The reaction mixture was quenched by 2 ml of sat. NH4Cl solution and then the organic layer was extracted with 7 ml of ethyl acetate. The combined organic layer was washed with 2 ml of sat. NH4Cl solution and 2 ml of sat. NaCl solution. Then the organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting compound was purified by column chromatography on Silica gel with EtOAc/hexane (1:2) solvent mixture as an eluant to give 36 mg of the title compound (I 1) (yield: 74%).

1. customprepared by the Step 1 in a dropwise manner at −79° C.
2. stirringthe mixture was stirred at 0° C. for 3 hrs
3. customThe reaction mixture was quenched by 2 ml of sat. NH4Cl solution
4. extractionthe organic layer was extracted with 7 ml of ethyl acetate
5. washThe combined organic layer was washed with 2 ml of sat. NH4Cl solution and 2 ml of sat. NaCl solution
6. dry with materialThen the organic layer was dried over anhydrous MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe resulting compound was purified by column chromatography on Silica gel with EtOAc/hexane (1:2) solvent mixture as an eluant

ORD record

ord-54550588d2014677a611cd807dcb5bfe

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07723376B2