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Chemical Structure| 949495-11-8 Chemical Structure| 949495-11-8

Structure of 949495-11-8

Chemical Structure| 949495-11-8

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Product Details of [ 949495-11-8 ]

CAS No. :949495-11-8
Formula : C15H19NO5
M.W : 293.32
SMILES Code : O=C(N1C[C@H](C(OCC)=O)[C@@H](O)C1)OCC2=CC=CC=C2

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Application In Synthesis of [ 949495-11-8 ]

* 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 [ 949495-11-8 ]

[ 949495-11-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 51814-19-8 ]
  • [ 949495-11-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;dichloro(benzene)ruthenium(II) dimer; (S)-binap; In dichloromethane; at 50 - 102℃; under 37503.8 Torr; for 5.16667h; [Example 1] Synthesis of 1-benzyl 3-ethyl (3S,4R)-4-hydroxypyrrolidine-1,3-dicarboxylate; [Show Image] 90 mL of dehydrated N,N-dimethylformamide was added to 2.58 g of benzene ruthenium (II) chloride dimer (5.15 mmol) and 6.73 g of (S)-(-)-2,2,'-bis(diphenylphosphino)-1,1-binaphthyl (S-BINAP) (10.8 mmol). The mixture was stirred for 10 minutes in an oil bath at an external temperature of 97 to 102C in an argon atmosphere. Subsequently, the mixture was stood to be cooled at room temperature. Volatile materials were evaporated under reduced pressure in an oil bath at an external temperature of 50 to 60C to give a catalyst. 300 g of <strong>[51814-19-8]1-benzyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate</strong> (1.03 mol) and 500 mL of dehydrated dichloromethane were placed in an autoclave and the ruthenium catalyst dissolved in 850 mL of dehydrated dichloromethane was added. The mixture was stirred for 6 hours under a hydrogen pressure of 5 MPa at an external temperature of 50 to 62C. Hydrogen was released and the reaction mixture was concentrated under reduced pressure. This gave 320 g of the title compound as a green oil. This product was used in the subsequent step without further purification. 1H-NMR (CDCl3, 400 Mz) delta: 1.27 (3H, t, J = 7.1 Hz), 2.31-2.40 (1H, m), 2.96-3.10 (1H, m), 3.36 (1H, ddd, J = 12.0, 5.4, 2.7 Hz), 3.66 (1H, dd, J- 11.2, 7.1 Hz), 3.76-3.87 (2H, m), 4.19 (2H, q, J = 7.1 Hz), 4.56-4.59 (1H, m), 5.14 (2H, s), 7.29-7.37 (5H, m). CI-MS (positive): m/z 294 [M+H]+
  • 2
  • [ 51814-19-8 ]
  • [ 949495-17-4 ]
  • [ 949495-11-8 ]
  • C15H19NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(benzene)ruthenium(II) dimer; hydrogen; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In dichloromethane; at 60 - 65℃; under 7500.75 - 9750.98 Torr; for 8h;Inert atmosphere; General procedure: Reference Examples 3 to 7 [0269] A dichlorobenzene ruthenium(II) dimer (172 mg, 0.34 mmol), (S)-(-)-BINAP (428 mg, 0.69 mmol), and dichloromethane (3.7 mL) were added, followed by stirring at an outer temperature of from 60 C. to 65 C. for 0.5 hours and then cooling to a temperature of approximately room temperature. [0270] To a mixture were added a <strong>[51814-19-8]1-benzyl 3-ethyl 4-oxopyrrolidine-1,3-dicarboxylate</strong> (5.0 g, 17.2 mmol) and dichloromethane (15 mL) under an argon atmosphere, followed by stirring at an internal temperature of from 60 C. to 65 C. for 8 hours under hydrogen pressurization. The HPLC measurement of this reaction mixture was carried out. The results are shown in Table 11.
 

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