Benzaldehyde → (S)-3-Benzylideneamino-2-oxo-1-piperidineacetic acid, Ethyl ester

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Reaction Steps

To a solution of 22 (4.7586 g, 0.0200 mol) and benzaldehyde (2.1224 g, 0.0200 mol, 2.03 mL) in 50 mL CH2Cl2 at 0° under N2 was added anhydrous MgSO4 (5.0 g) and Et33N (4.05 g, 0.040 mol, 5.58 mL). The mixture was stirred from 0° to ambient temperature over 21 hrs, filtered under N2, and the solvent was evaporated. The residue was dissolved in 300 mL of diethyl ether, extracted with 50 mL portions of water (3×), brine, dried over MgSO4, filtered under N2 and evaporated to afford 5.13 g (89% yield) of product 23 as a light yellow viscous oil. The material was hydrolytically labile and was stored at 0° under a N2 atmosphere.

Provenance & Evidence