Sodium hydride → HCID 57954443, compound

HRID 221340Notes

Reaction equation

HRID 221340 reaction equation
[H-].[Na+].[OH:3][NH:4][C:5](=[NH:12])[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.C[O:14][C:15]([C@H:17]1[CH2:21][CH2:20][C@@H:19]([CH2:22]O)[CH2:18]1)=O>C1COCC1>[N:9]1[CH:10]=[CH:11][C:6]([C:5]2[N:12]=[C:22]([C@@H:19]3[CH2:20][CH2:21][C@H:17]([CH2:15][OH:14])[CH2:18]3)[O:3][N:4]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 57351148HCID 57351148, compoundHCID 178513374HCID 178513374, compound

Product 1

HCID 57954443HCID 57954443, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (10 mg of a 60% dispersion in oil, 2.5 mmol) was added to a solution of N-hydroxyisonicotinamidine (344 mg, 2.5 mmol) in anhydrous THF (3 ml) and the mixture heated under reflux for 1 h. cis-Methyl-3-hydroxymethylcyclopentane-1-carboxylate (396 mg, 2.5 mmol) was added in one portion and heating was continued for 18 h. After cooling, the solution was filtered through celite and the filtrate concentrated in vacuo. The residue was purified by flash chromatography (IH-EtOAc, 1:1 to 0:1) to afford the title compound: RT=2.59 min, m/z (ES+)=246.1 [M+H]+.

Workup

  1. temperaturethe mixture heated
  2. additionwas added in one portion
  3. temperatureheating
  4. temperatureAfter cooling
  5. filtrationthe solution was filtered through celite
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified by flash chromatography (IH-EtOAc, 1:1 to 0:1)

Sources & evidence

ORD record
ord-5d03f210b0a4467d84ba5af5769af7f0
Source dataset
uspto-grants-2012_06
Patent number
US08207147B2

Reaction notes

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