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Chemical Structure| 145530-80-9 Chemical Structure| 145530-80-9

Structure of 145530-80-9

Chemical Structure| 145530-80-9

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Product Details of [ 145530-80-9 ]

CAS No. :145530-80-9
Formula : C15H21NO4
M.W : 279.33
SMILES Code : O=C(OC(C)(C)C)C1C=CC=C(C(=O)OC(C)(C)C)N=1
English Name :Di-tert-butyl pyridine-2,6-dicarboxylate
MDL No. :N/A

Safety of [ 145530-80-9 ]

Application In Synthesis of [ 145530-80-9 ]

* 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 [ 145530-80-9 ]

[ 145530-80-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 145530-80-9 ]
  • [ 868769-75-9 ]
YieldReaction ConditionsOperation in experiment
83% With methanol; sodium tetrahydroborate; sodium methylate at 20℃; for 3h; Inert atmosphere; Tert butyl-6-(hydroxymethyl)-2-carboxylate pyridine. Compound 6 was synthesized following a modified literature procedure. [18,19] Under N2 gas was added 5 (17.984 g, 1.00 eq, 0.0644 mol), and sodium methoxide (0.1739 g, 0.05 eq, 0.0032 mol) were dissolved in 300 mL MeOH and stirred at room temperature for 15 min. Sodium borohydride (3.653 g, 1.50 eq, 0.0966 mol) was added and the solution was stirred for 3 h. The reaction was quenched with the addition of 150 mL saturatedsodium bicarbonate solution and poured over 200 mL DCM. The organic layer was extracted, and the aqueous layer was further extracted with DCM (3 × 50 mL). The collected organic layers were dried and evaporated to a brown oil. The crude product was purified via column chromatography 2-8 % MeOH in DCM. Product fractions were determinedfrom TLC, combined and evaporated to yield a white powder (11.181 g, 83 %). 1H NMR (598 MHz, CDCl3) δ 7.93 (d, J =7.7 Hz, 1H), 7.80 (t, J = 7.7 Hz, 1H), 7.44 (d, J = 7.9 Hz, 1H), 4.83 (d, J = 5.0 Hz, 2H), 3.83 (s, 1H), 1.62 (s, 9H). 13C NMR (151 MHz, CDCl3) δ 163.92, 159.72, 148.34, 137.48, 123.42, 123.40, 82.30, 64.30, 28.10.
72% With sodium tetrahydroborate In methanol at 0 - 20℃;
72% With methanol; sodium tetrahydroborate at 0 - 20℃;
72 % With sodium tetrahydroborate In methanol at 20℃;

  • 2
  • [ 145530-80-9 ]
  • [ 889858-16-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 0 - 20 °C 2: selenium(IV) oxide / 1,4-dioxane / 100 °C
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 20 °C 2: selenium(IV) oxide / 1,4-dioxane / 12 h / 100 °C
 

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