Potassium Sodium Tartrate → HCID 68535289, compound

Participants

Reaction Steps

To a solution of tert-butyl 4-[4-(methoxycarbonyl)-1,3-oxazol-2-yl]-1H-indole-1-carboxylate (512 mg) in DCM (10.2 mL) was added dropwise 1M DIBAL in DCM solution (4.2 mL) at 0° C. and the mixture was stirred at the same temperature for 1.5 hours. 1M DIBAL in DCM solution (0.60 mL) was added dropwise to the mixture. The mixture was stirred at 0° C. for 1.5 hours. To the resulting solution was added dropwise 1M Rochelle salt aqueous solution (25.0 mL) and the suspension was stirred at ambient temperature for overnight. The suspension was diluted with chloroform (50.0 mL) and filtered through a bed of celite. The layers were separated and the organic layer was washed with 0.5 M Rochelle salt solution, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silica gel column chromatography (n-hexane:EtOAc=2:1) to give tert-butyl 4-[4-(hydroxymethyl)-1,3-oxazol-2-yl]-1H-indole-1-carboxylate.

Provenance & Evidence