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Chemical Structure| 2259698-26-3 Chemical Structure| 2259698-26-3

Structure of 2259698-26-3

Chemical Structure| 2259698-26-3

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Product Details of [ 2259698-26-3 ]

CAS No. :2259698-26-3
Formula : C14H20N2O3
M.W : 264.32
SMILES Code : O=C(N(C1)CC2=C1C(C)=C(C)NC2=O)OC(C)(C)C
English Name :tert-Butyl 6,7-dimethyl-4-oxo-1,3,4,5-tetrahydro-2H-pyrrolo[3,4-c]pyridine-2-carboxylate
MDL No. :MFCD32661944

Safety of [ 2259698-26-3 ]

Application In Synthesis of [ 2259698-26-3 ]

* 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.

  • Downstream synthetic route of [ 2259698-26-3 ]

[ 2259698-26-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 24424-99-5 ]
  • [ 78-93-3 ]
  • [ 175463-32-8 ]
  • [ 2259698-26-3 ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: butanone; 3-cyano-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester With polyphosphoric acid at 100 - 120℃; for 4h; Stage #2: di-<i>tert</i>-butyl dicarbonate In water at 15℃; for 15h; P1.1 Step 1. Synthesis of ten-butyl 6, 7-dimethyl-4-oxo-1,3,4,5-tetrahydro-2H- pyrrolo[3, 4-c]pyridine-2-carboxylate ( C1). A mixture of fe/f-butyl 3-cyano-4-oxopyrrolidine-1 -carboxylate (5.00 g, 23.8 mmol) in butan-2-one (20 mL) was added to polyphosphoric acid (100 g) at 100 °C, and the reaction mixture was stirred at 100 °C to 120 °C for 4 hours. After the reaction mixture had been cooled to 15 °C, it was quenched via addition of water (1 .5 L), and the pH of the mixture was adjusted to 10 - 1 1 using solid sodium hydroxide. Di-fe/f-butyl dicarbonate (10.0 g, 45.8 mmol) was added, and the reaction mixture was stirred for 15 hours at 15 °C, whereupon it was filtered. The collected solid was washed sequentially with water (7 x 50 mL) and with a mixture of fe/f-butyl methyl ether and petroleum ether (1 : 1 ; 7 x 40 mL) to afford the product as an off-white solid. From analysis of the 1 H NMR, this material was presumed to exist as a mixture of rotamers. Yield: 4.0 g, 15 mmol, 63%. LCMS m/z 264.8 [M+H]+. 1H N MR (400 MHz, CDCI3) δ 12.6-12.5 (br s, 1 H), 4.65-4.48 (m, 4H), 2.32 (s, 3H), 1 .97 (s, 3H), [1 .52 (s) and 1 .51 (s), total 9H].
  • 2
  • [ 24424-99-5 ]
  • [ 175463-32-8 ]
  • [ 2259698-26-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: tert-butyl 3-cyano-4-oxopyrrolidine-1-carboxylate In butanone at 100 - 120℃; for 4h; Stage #2: di-<i>tert</i>-butyl dicarbonate With sodium hydroxide In water; butanone at 15℃; 1.1 tert-Butyl 6,7-dimethyl-4-oxo-1,3,4,5-tetrahydro-2H-pyrrolo[3,4-c]pyridine-2-carboxylate To a mixture of 1a (5 g, 23.8 mmol) and 2-butanone (20 mL) was added polyphosphoric acid (100 g) at 100 ° C., and then the mixture was heated to 120 ° C. and stirred for 4 hours. After the reaction mixture was cooled to 15 ° C., water (1.5 L) was added to quench it, and solid sodium hydroxide was added to adjust the pH of the mixture to 10-11. Di-tert-butyl dicarbonate (10 g, 45.8 mmol) was added, and the reaction mixture was stirred at 15 ° C. overnight and filtered after the reaction was completed. The collected solid was washed with water (7 x 50 mL), a mixture of tert-butyl methyl ether and petroleum ether (1: 1, 7 x 40 mL) to give the crude product Example 1b.
 

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