5-Oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid

Methyl 1-benzyl-5-oxo-3-pyrrolidinecarboxylate (2.00 g, 8.57 mmol) was dissolved in a mixed solvent of methanol (10 ml) and tetrahydrofuran (10 ml), followed by adding thereto a 2N aqueous lithium hydroxide solution (8.6 ml, 17.2 mmol), and the resulting mixture was heated under reflux for 20 minutes. After completion of the reaction, the reaction solution was ice-cooled, made into an acidic solution with an aqueous potassium hydrogensulfate solution, and then extracted with ethyl acetate. The ethyl acetate layer was concentrated, washed by repulping (ethyl acetate/hexane), and then dried to obtain 1-benzyl-5-oxo-3-pyrrolidinecarboxylic acid (1.83 g, 97percent).1H-NMR (DMSO-d6) δ; 2.56 (2H, m), 3.80 (1H, m), 3.15 (2H, m), 3.25 (2H, m), 4.36 (2H, q, J=8.6Hz), 7.27 (5H, m), 12.61 (1H, s).A solution of itaconic acid (18 g, 0.138 mol)And thiamine (14.8 g, 0.138 mol) in a reaction flask, N2 protection, Heated to 130 ° C, Stirring slowly after melting, Reaction 2.5h, Stop heating, When cooled to 100 ° C, 200 ml of a 10percent NaOH solution was added under stirring, Cooled to room temperature, The aqueous layer was washed with ethyl acetate, Was added dropwise to the aqueous layer with 10percent hydrochloric acid solution, A large number of white solid generation, To & lt; RTI ID = 0.0 & gt; 1, Washed to a pH of about 6, A white granular solid 25. lg, The yield was 82.9percentMp 143-145 ° C, HRMS = 220.0886 [M + H] & lt; + & gt ;.

Molecular Weight:219.24
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:219.08954328
Monoisotopic Mass:219.08954328
Topological Polar Surface Area:57.6
Heavy Atom Count:16
Complexity:284
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes