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0 °C

3-Methyl-4-oxo-piperidine-1,3-dicarboxylic acid-1-tert-butyl ester 3-methyl ester (1.1 g, 4.07 mmol) was dissolved in tetrahydrofuran and cooled to 0° C. To the solution was added 4-chlorophenyl magnesium bromide (12.2 mL, 12.2 mmol) dropwise over ˜½ h and then stirred at 0° C. for 1 h. The reaction was quenched with saturated solution of NH4Cl and extracted with ethyl acetate (3×). The organics were collected, dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (10% ethyl acetate/90% hexane to 20% ethyl acetate/80% hexane) to yield the title compound (1.1 g, 70%). 1H-NMR (CDCl3): δ 1.17 (s, 3H), 1.44 (s, 9H), 1.55 (m, 1H), 1.96 (d, 1H) 3.00 (m, 1H), 3.37 (m, 2H), 3.53 (s, 3H), 3.91 (m, 2H), 4.07 (d, 1H), 7.27 (d, 2H), 7.43 (d, 2H). ESI-MS m/z: 384.1 (M+1), retention time 2.95.

1. customThe reaction was quenched with saturated solution of NH4Cl
2. extractionextracted with ethyl acetate (3×)
3. customThe organics were collected
4. dry with materialdried over Mg2SO4
5. filtrationfiltered
6. customevaporated in vacuo
7. custompurified by Biotage flash chromatography (10% ethyl acetate/90% hexane to 20% ethyl acetate/80% hexane)