Water → 1-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-cyclopropylamine

HRID 1040453Notes

Reaction equation

HRID 1040453 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]#[N:13])[N:9]=[CH:8]1.[CH3:16][CH2:17][Mg+].[Br-].O>C1COCC1.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[C:10]([C:12]2([NH2:13])[CH2:17][CH2:16]2)[N:9]=[CH:8]1

Participants

6

Reactant 3

HCID 962WaterHCID 584311371-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrileHCID 178461630HCID 178461630, compound

Product 1

HCID 584311581-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-cyclopropylamineYield 49.5%

Reagents, catalysts & solvents 2

HCID 178460666HCID 178460666, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a round bottom flask was added 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile (310 mg, 3.19 mmol) in THF (10 ml), followed by the addition Ti(OiPr)4 (0.9 ml, 3.05 mmol) Next, EtMgBr (3.0 M in ether) (1.85 ml, 5.55 mmol) was added slowly. The clear solution changed to dark and gas evolved was found. The reaction mixture was stirred at room temperature for 0.5 h. The reaction mixture was added with water (10 ml). The solid precipitate was filtered through celite. The filter cake was washed with THF (10 ml), EtOAc (10 ml). The combined solvent was concentrated to afford 400 mg of 1-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-cyclopropylamine, m/z 254.6 [M+1]+.

Workup

  1. additionwas added slowly
  2. filtrationThe solid precipitate was filtered through celite
  3. washThe filter cake was washed with THF (10 ml), EtOAc (10 ml)
  4. concentrationThe combined solvent was concentrated

Sources & evidence

ORD record
ord-2078c1750f0b4ad291fb0e4ed32971c3
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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