Tetrabutylammonium Fluoride → HCID 57637341, compound

Participants

Reaction Conditions

Reaction Steps

To 2-(1-tert-butoxycarbonyl-5-piperidin-1-ylmethyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-(tert-butyl-dimethyl-silanyloxymethyl)-indole-1-carboxylic acid tert-butyl ester [530 mg, 0.78 mmol, Intermediate (83)] in tetrahydrofuran (10 mL) at 0° C. was added a 1M solution of TBAF in tetrahydrofuran (0.86, 0.86 mmol). The mixture was stirred at 0° C. for 2 hours. It was diluted with ethyl acetate and washed with saturated aqueous ammonium chloride. The organic layer was dried over magnesium sulfate and concentrated. The residue was chromatographed through silica gel (n-heptane/ethyl acetate, 80/20 as eluant) to afford 2-(1-tert-butoxycarbonyl-5-piperidin-1-ylmethyl-1H-thieno[3,2-c]pyrazol-3-yl)-5-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester [305 mg, 70%, Intermediate (84)] as a white foam. LC/MS: 567.3 (M+H), RT=2.89 minutes.

Provenance & Evidence