Potassium Carbonate → tert-Butyl 4-ethynyl-5,6-dihydropyridine-1(2H)-carboxylate

HRID 727088Notes

Reaction equation

HRID 727088 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH:18]=[C:17]([C:20]#[C:21][Si](C)(C)C)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>CO>[C:7]([O:11][C:12]([N:14]1[CH2:15][CH:16]=[C:17]([C:20]#[CH:21])[CH2:18][CH2:19]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 18942192tert-Butyl 4-[(trimethylsilyl)ethynyl]-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 18942198tert-Butyl 4-ethynyl-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (1.0 g, 7.2 mmol) was added to a solution of 1-tert-butoxycarbonyl-4-trimethylsilylethynyl- 1,2,3,6-tetrahydropyridine (44.9 g, 16 lmmol) in methanol (250 ml) under a nitrogen atmosphere and the mixture was stirred at room temperature for 3 hours. The solution was evaporated in vacuo without heating. The residue was dissolved in ether (250 ml), washed with sodium carbonate (sat., 100 ml), water (50 ml) and brine (50 ml) before drying (MgSO4) and evaporation in vacuo to give the title compound as a white waxy solid (30.0 g, 90%); δH (CDCl3) 1.46 (9H, s, OC(CH3)3), 2.24-2.26 (2H, m, tetrahydropyridinyl CH2), 2.89 (1H, s, ethynyl CH), 3.49 (2H, t, J 5.7 Hz, tetrahydropyridinyl CH2), 3.95-3.97 (2H, m, tetrahydropyridinyl CH2) and 6.10 (1H, s, tetrahydropyridinyl CH).

Workup

  1. customThe solution was evaporated in vacuo
  2. temperaturewithout heating
  3. dissolutionThe residue was dissolved in ether (250 ml)
  4. washwashed with sodium carbonate (sat., 100 ml), water (50 ml) and brine (50 ml)
  5. custombefore drying
  6. custom(MgSO4) and evaporation in vacuo

Sources & evidence

ORD record
ord-e336d67b6f634052b07637b345e8cefb
Source dataset
uspto-grants-1998_01
Patent number
US05712285

Reaction notes

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