Sodium borohydride → 4-[2-(Tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-one

Participants

Reaction Steps

A solution of 5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methyl-benzyl)-1-propyl-imidazolidine-2,4-dione (14.71 g, 27.8 mmol) in EtOH (500 mL) was treated with sodium borohydride (15.78 g, 0.417 mol) in three portions over 6 h and stirred at room temperature under N2 for an additional 16 h. The thick reaction mixture was cooled in an ice bath and slowly quenched with aqueous 1 N HCl (˜1 L) over a 1 h period. The reaction mixture was then worked up extractively with EtOAc, water and brine and the organic layer dried (MgSO4) and the solvent removed in vacuo to give 16.79 g crude 4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(4-methyl-benzyl)-3-propyl-1,3-dihydro-imidazol-2-one that was de-silylated immediately.

Provenance & Evidence