Sodium ethoxide → HCID 178451642, compound

HRID 510219Notes

Reaction equation

HRID 510219 reaction equation
O=[C:2]1[CH:7]([C:8](OCC)=[O:9])[CH2:6][CH2:5][N:4]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:3]1.Cl.[CH:21]([NH2:23])=[NH:22].CC[O-].[Na+]>CCO>[OH:9][C:8]1[C:7]2[CH2:6][CH2:5][N:4]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:3][C:2]=2[N:22]=[CH:21][N:23]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 158529891-tert-Butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate

Product 1

HCID 178451642HCID 178451642, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-tert-butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate (2.00 g, 7.39 mmol) in EtOH (37 mL) was added formamidine hydrochloride (910 mg, 11.08 mmol) followed by NaOEt (6.89 mL, 2.68 M in EtOH) dropwise. The mixture was then heated to reflux overnight. The mixture was concentrated in vacuo and then dissolved in a minimum amount of water. The pH was adjusted to pH 7 with 1 N HCl. The aqueous layer was then saturated with solid NaCl and extracted with a combination of EtOAc and DCM. The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography on SiO2 eluting with IPA/EtOAc afforded the desired product as a white solid (993 mg, 53%). MS (ESI) mass calcd. C12H12N3O3, 251.13. m/z found 252.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 8.05 (s, 1H), 4.42 (s, 2H), 3.69-3.61 (m, 2H), 2.63 (s, 2H), 1.49 (s, 9H).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutiondissolved in a minimum amount of water
  5. extractionsaturated with solid NaCl and extracted with a combination of EtOAc and DCM
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-536af83cdeb646818b592c23ba621b59
Source dataset
uspto-grants-2015_08
Patent number
US09096596B2

Reaction notes

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