Structure of 42599-26-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 42599-26-8 |
Formula : | C5H7NO2 |
M.W : | 113.11 |
SMILES Code : | O=C1N(C)CCC1=O |
MDL No. : | MFCD11868754 |
InChI Key : | DHFODCCTNFXCCQ-UHFFFAOYSA-N |
Pubchem ID : | 12211348 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Ethyl l-methyl-4,5-dioxo-3-pyrrolidinecarboxylate B.45 (6.76g, 33.6ommol) [Southwick, P. L., E. P. Previc, et al. (1956). J. Ore. Chem. 21(10): 1087-1095.] was dissolved in 76ml of acetic acid and 1 ImI of 48% by weight HBr. The solution was heated to a gentle reflux for 1 hour. The reaction was then poured into 400ml of ice and stirred until the ice melted. The aqueous layer was extracted with chloroform. The pH of the aqueous layer was adjusted to ~7 with sat. NaHCO3 was and then extracted with dichloromethane. The organic layer was dried over MgSO4 then concentrated under vacuum. The residue was triturated with ether and filtered to remove solids. The filtrates were concentrated under vacuum to give a reddish oil which was purified by CombiFlash chromatography eluting with acetonitrile/0.1% TFA. The fractions containing the product were concentrated under vacuum to give l-methyl-2,3- pyrrolidinedione B.46 (214mg,).IH NMR (500 MHz, DMSO-d6) δ ppm 3.56 (2 H, t, J=5.4 Hz), 2.97 (3 H, s), 2.62 (2 H, t, J=5.5 Hz) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In tetrahydrofuran; at 65℃; for 4.0h; | A 20 L round-bottomed flask equipped with an overhead stirrer was charged with 4-hydroxy-1-methyl-5-oxo-2,5-dihydro-1H- pyrrole-3-carboxylic acid (1000 g, 6.360 mol) and THF (15 L). The resultant mixture was heated to 65 C. After 4 h, the mixture was concentrated to dryness to give 1- methylpyrrolidine-2,3-dione (712 g, 99%) as a yellow solid.1H NMR (400 MHz, CDCl3) d 3.70 (t, J = 5.7 Hz, 2H), 3.13 (s, 3H), 2.72 (t, J = 5.7 Hz, 2H). |
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