Imidazole → HCID 59614329, compound

Participants

Reaction Steps

To a solution of ((1R,3S)-1-ethyl-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester (0.541 mmol; 124 mg) and imidazole (2.164 mmol; 147 mg) in DMF (1.8 mL) is added tert-butyldimethylsilyl chloride (1.623 mmol; 245 mg) at room temperature under N2. After 12 hours, the reaction mixture is quenched with water, extracted three times with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtered, concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc) to give [(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-1-ethyl-pent-4-enyl]-carbamic acid tert-butyl ester (160 mg, 86%); ESI-MS m/z: 288 [M+−tBu+2], Retention time 5.77 min (condition B).

Provenance & Evidence