Imidazole → HCID 59468942, compound

Participants

Reaction Steps

To a solution of 2-methyl 1-(phenylmethyl) (2R,5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-1,2-pyrrolidinedicarboxylate (D71, 200 mg, 0.4 mmol) and imidazole (60 mg, 0.88 mmol) in dry DMF (1 ml) was added tert-butyl dimethylsilyl chloride and the mixture was stirred for 36 hours. The reaction was quenched with brine, diluted with water and extracted with ethyl acetate. The organic layer was washed with ice cold brine, dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel using cyclohexane and ethyl acetate (1:0 to 9:1) to afford the title compound as a colourless oil (180 mg, 74%); Rt (HPLC): 8.50 min; MS: (ES/+) m/z: 608 [MH]+ C34H42FNO6Si requires 607.

Provenance & Evidence