Imidazole → HCID 178455372, compound

HRID 245991Notes

Reaction equation

HRID 245991 reaction equation
[OH:1][C@@H:2]1[CH2:5][C@H:4]([C:6]#[N:7])[CH2:3]1.N1C=CN=C1.[CH3:13][C:14]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C=O)C>[Si:17]([O:1][C@@H:2]1[CH2:5][C@H:4]([C:6]#[N:7])[CH2:3]1)([C:14]([CH3:16])([CH3:15])[CH3:13])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178511297HCID 178511297, compound

Product 1

HCID 178455372HCID 178455372, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of cis-3-hydroxy-cyclobutanecarbonitrile (500 mg, 5.15 mmol in DMF (3 mL) at room temperature was added imidazole (876 mg, 12.9 mmol) followed by TBDMS-Cl (854 mg, 5.66 mmol). The reaction mixture was stirred at room temperature overnight then quenched with water and extracted with EtOAc (2×). The combined organics were washed with water (3×), dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography with 0% to 10% EtOAc/hexanes to afford 890 mg (82%) of cis-3-(tert-butyldimethylsilanyloxy)-cyclobutanecarbonitrile as a colorless oil. 1H NMR (CDCl3, 400 MHz): δ (ppm) 4.10-4.19 (m, 1H), 2.57-2.67 (m, 2H), 2.43-2.54 (m, 1H), 2.22-2.34 (m, 2H), 0.84 (s, 9H), 0.00 (s, 6H).

Workup

  1. customthen quenched with water
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organics were washed with water (3×)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography with 0% to 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-05cbc5bf64574da48adc6718be8fb6e4
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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