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Chemical Structure| 1169762-29-1 Chemical Structure| 1169762-29-1

Structure of 1169762-29-1

Chemical Structure| 1169762-29-1

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Product Details of [ 1169762-29-1 ]

CAS No. :1169762-29-1
Formula : C12H24N2O2
M.W : 228.33
SMILES Code : O=C(OC(C)(C)C)NC1(CC)CNCCC1
MDL No. :MFCD14582326

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Application In Synthesis of [ 1169762-29-1 ]

* 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 [ 1169762-29-1 ]

[ 1169762-29-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 913543-99-4 ]
  • [ 747392-34-3 ]
  • [ 1169762-29-1 ]
  • C27H38BrFN4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A mixture of 14 (5.00 g; 20.4 mmol) and 13a (4.37 g; 20.4 mmol) in CH3CN (60 ml) was stirred at 50 C for 1 h. After cooling to room temperature, 1,8-diazabicyclo[5,4,0]undeca-7-ene (DBU) (6.20 g; 40 mmol) and 2-bromo-5-fluoro-benzylamine (4.99 g; 24.4 mmol) were added to the mixture, and the resulting mixture was stirred at 80 C for 10 h. After removal of the solvent, the residue was diluted with EtOAc, and washed with H2O, 10%KHSO4 aq, 10%NaOH aq and brine. The EtOAc layer was dried over Na2SO4 and the filtrate was concentrated. The residue was dissolved in DMF (60 mL), and ethyl bromoacetate (2.80 mL; 28 mmol) and K2CO3 (8.5 g) were added. The resulting slurry was then stirred at 50 C for 2 h and cooled to room temperature. The slurry was diluted with EtOAc, filtered through Celite, and washed with satd NH4Cl aq and brine. The organic layer was dried over Na2SO4, and the filtrate was concentrated. To tert-butyl alcohol (30 mL) was added lithium amide (1.16 g; 48 mmol). After stirring at 80 C for 1 h, the resulting mixture was cooled to 30 C, and CH3CN (40 mL) was added. A solution of the alkylated product from the third step in toluene (10 mL) was next added dropwise, and the reaction mixture was stirred for 2 h at 30 C. The solvent was removed, and to the residue was added EtOAc. The resulting mixture was finally washed with satd NH4Cl aq and brine, the organic layer was dried over Na2SO4, and the filtrate was concentrated. The residue was purified by SiO2 column chromatography (Hexane/EtOAc = 6/1 to 3/1) to give 5.80 g (44% from 14) of 15a as amorphous solid. In addition to the target product 15a, the ester exchange product (R2 = tert-butyl) was also obtained as an amorphous (415 mg).
 

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