Ethyl 2-((S)-1-phenylethylamino)acetate, 2. To a stirred solution of (S)phenylethylamine (1 g, 7.8 mmol, 1 eq) in 40 mL of CH 3 CN was added the ethyl 2bromoacetate (0.865 mL, 7.8 mmol, 1 eq) and K 2 CO 3 (2.15 g, 15.6 mmol, 2 eq).The reaction mixture was stirred for 2 h at room temperature. Finally, the mixture was filtered and the solvent was evaporated under reduced pressure. The crude
In the title compound, C17H22N2O4S, a thiopiperidine derivative, the piperidine ring has an envelope conformation with the methylene C atom opposite to the C=S bond as the flap. The nitromethyl substituent is equatorial while the ethoxycarbonyl group is axial. The mean planes of the nitromethyl group, the carboxy group and phenyl ring are inclined to the mean plane through the five planar atoms of the piperidine ring [maximum deviation = 0.070 (4) Å] by 56.8 (2), 83.8 (5) and 87.1 (2)°, respectively. There is an intramolecular C—H⋯O hydrogen bond involving an H atom of the ethoxycarbonyl group and a nitro O atom. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming chains along [100]. The chains are linked by further C—H⋯O hydrogen bonds, forming corrugated layers lying parallel to (001).
Diastereoselective Approach to cis-4-Methyl/Thiol-Pipecolic Esters Based on RCM Reaction and Conjugate Michael Addition. -An efficient method for the diastereoselective synthesis of cis-4-methyl-as well as cis-4-mercaptopipecolic acid esters [cf. (XII)] starting from (S)-phenylethylamine is developed. -(ZARATE, A.; OREA, L.; JUAREZ, J. R.; CASTRO, A.; MENDOZA, A.; GNECCO, D.; TERAN*, J. L.; Synth.
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