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(2S)-tert-butyl 2-methyl-4-oxo-5-(pyrimidine-2-carbonyl)piperidine-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
73.47%
To a mixture of (S)-tert-butyl 2-methyl -4-oxopiperidine-1-carboxylate (5 g, 23.44 mmol) in THF (40 mL) was added LiHMDS (1 M, 46.88 mL) in one portion at 0 C under N2. The reaction mixture was stirred at 0 C for 0.5 h, then methyl pyrimidine-2-carboxylate (5.50 g, 39.85 mmol) in THF (40 mL) was added into the solution at 0 C and stirred at 15 C for 4 hours. The reaction mixture was poured into aq. NH4CI (200 mL) and stirred for 1 min. The aqueous phase was extracted with ethyl acetate (200 mL/2). The organics layers were separated, washed with brine (100 mL/2). dried with anhydrous NaaSCL, fdtered and concentrated in vacuum. Purification (FCC, S1O2, Petroleum ether/Ethyl acetate=l0/l to 0: 1) afforded (2S)-tert-butyl 2-methyl-4-oxo-5-(pyrimidine-2-carbonyl)piperidine-l-carboxylate (5.5 g, 17.22 mmol, 73.47% yield) as a yellow oil. MS (ESI): mass ealed. for C16H21N3O4, 319.2; m/z found, 342.1 [M+Na]+.
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