1,4(2H)-Pyridinedicarboxylic acid, 3,6-dihydro-, 1-(1,1-dimethylethyl) 4-ethyl ester synthesis
- Product Name:1,4(2H)-Pyridinedicarboxylic acid, 3,6-dihydro-, 1-(1,1-dimethylethyl) 4-ethyl ester
- CAS Number:906663-30-7
- Molecular formula:C13H21NO4
- Molecular Weight:255.31
71233-28-8
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Yield:906663-30-7 82 %
Reaction Conditions:
with 1H-imidazole;1,1'-(Azodicarbonyl)dipiperidin;trimethylphosphane in dichloromethane;toluene at 20;
Steps:
(E)-diazene-l,2-diylbis(piperidin-l-ylmethanone) (6.92 g, 27.4 mmol, 1.5 eq.) and IH-pyrrole (1.84 g, 27.4 mmol, 1.5 eq.) were added to a solution of l-(tert-butyl) 4-ethyl 3- hydroxypiperidine-l,4-dicarboxylate (5.0 g, 18.29 mmol, 1.0 eq.) in 280 mL of DCM at room temperature. Trimethylphosphane (36.6 mL, 36.6 mmol, 2.0 eq.) (1M solution in toluene) was then added dropwise and the reaction mixture was allowed to stirr for 48h. At this point TLC showed complete conversion of the starting material and a major product less polar (Rf=0.52 Hexanes/EtOAc 9: 1 ). Hexanes (200 mL) were added to the reaction mixture and the formed precipitate was filtrated. The filtrate was rinsed once with hexanes. l-(tert-Butyl) 4- ethyl 3,6-dihydropyridine-l,4(2H)-dicarboxylate was obtained by purification on FCC (Hexanes/AcOEt 100:0 to 70:30) as a yellow oil (3.81 g, 82%).
References:
WO2020/106627,2020,A1 Location in patent:Paragraph 00323
52763-21-0
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71233-25-5
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