Sodium Cyanide → HCID 178455424, compound

Participants

Reaction Conditions

Reaction Steps

The aldehyde (Intermediate A5) (10 g, 37.2 mmol) in anhydrous ethanol (70 mL) was treated with tosylmethyl isocyanide (7.2 g, 3.7 mmol) (available from Aldrich) followed by addition of a catalytic amount of NaCN (150 mg) at rt for 15 m. The mixture was reduced in volume to about 20 mL under reduced pressure. The residue was dissolved in NH3 (7M in MeOH) and placed into re-sealable tubes and heated to 100° C. for 18 h. The mixture was cooled and the solvent removed under vacuum. The residue was purified by flash chromatography on silica gel with 5% MeOH:EtOAc to remove TsOH and the product was eluted with 5% NH3-MeOH in CH2Cl2 to yield 7 g (60%) of 4-[3-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enylmethyl]-1H-imidazole (Intermediate A6).

Provenance & Evidence