Hydroxylamine → Methyl 2-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

HRID 646905Notes

Reaction equation

HRID 646905 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([CH:18]=O)[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[CH:9]=1)=[O:4].NO.[N:22]1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>CO.CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:18]#[N:22])[N:8]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:15])([CH3:16])[CH3:17])[CH:9]=1)=[O:4]

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 58638526methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate

Product 1

HCID 58638496Methyl 2-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-formyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carboxylic acid methyl ester (0.11 g, 0.38 mmol) (as prepared in the previous step) in methanol (2 mL) was added a 50% aqueous hydroxylamine solution (30 μL) and the reaction stirred for 3 h at RT and then concentrated. The residue was dissolved in DCM (2 mL), pyridine (0.13 mL), and trifluoroacetic anhydride (0.17 mL, 1.1 mmol) was added and the reaction stirred for 10 h at RT. The reaction was diluted with EtOAc (10 mL) and washed with satd. NaHCO3 (2×10 mL) and the organic layer dried over Na2SO4 and then concentrated. The title compound was eluted from a 10-g SPE cartridge (silica) with 30% EtOAc/hexane to give 0.085 g (76%) of a colorless oil. 1H-NMR (400 MHz, CDCl3): δ 7.99 (s, 1H), 5.50 (s, 2H), 3.92 (s, 3H), 3.58 (m, 2H), 0.94 (m, 214), 0.00 (s, 9H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in DCM (2 mL)
  3. stirringthe reaction stirred for 10 h at RT
  4. washwashed with satd
  5. dry with materialNaHCO3 (2×10 mL) and the organic layer dried over Na2SO4
  6. concentrationconcentrated
  7. washThe title compound was eluted from a 10-g SPE cartridge (silica) with 30% EtOAc/hexane

Sources & evidence

ORD record
ord-8fa4a9388e4e4b5081d7af586844cf91
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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