Isoamyl Nitrite → HCID 69527459, compound

HRID 1829815Notes

Reaction equation

HRID 1829815 reaction equation
N(OCCC(C)C)=O.N[C:10]1[N:14]([C@H:15]([CH2:19][OH:20])[C@@H:16]([OH:18])[CH3:17])[CH:13]=[N:12][C:11]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]>O1CCCC1>[OH:18][C@@H:16]([CH3:17])[C@H:15]([N:14]1[CH:10]=[C:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[N:12]=[CH:13]1)[CH2:19][OH:20]

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 69527450HCID 69527450, compound

Product 1

HCID 69527459HCID 69527459, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a refluxing solution of isoamyl nitrite (1.5 mL) in tetrahydrofuran (4.6 mL) was added a solution of ethyl 5-amino-1-[(1R,2S)-2-hydroxy-1-(hydroxymethyl)propyl]-1H-imidazole-4-carboxylate (0.92 g) in tetrahydrofuran (23 mL) dropwise over 45 minutes, and the mixture was refluxed for 75 minutes. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography on silica gel (gradient elution; 10:1 to 5:1 chloroform-1% ammonium hydroxide/methanol) to give ethyl 1-[(1R,2S)-2-hydroxy-1-(hydroxymethyl)propyl]-1H-imidazole-4-carboxylate (0.50 g).

Workup

  1. temperaturethe mixture was refluxed for 75 minutes
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (gradient elution; 10:1 to 5:1 chloroform-1% ammonium hydroxide/methanol)

Sources & evidence

ORD record
ord-29b8fb8a574945999eebf367f174d203
Source dataset
uspto-grants-2006_06
Patent number
US07064144B2

Reaction notes

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