Allyl iodide → HCID 66688630, compound

Participants

Reaction Steps

5-(3-Allyl-pyrrolidine-3-carbonyl)-indazole-1-carboxylic acid tert-butyl ester was prepared as described in steps 3 and 4 of Example 1, but replacing benzyl bromide with allyl iodide. Pd/C (10%, Degussa catalyst type E101 NE/W, 100 mg) was added to a solution of 5-(3-allyl-pyrrolidine-3-carbonyl)-indazole-1-carboxylic acid tert-butyl ester (200 mg, 0.56 mmol) in MeOH (10 mL). The resulting mixture was stirred under hydrogen atmosphere (balloon pressure) for 2.5 hours. The reaction mixture was then filtered through a celite pad and the filtrate was evaporated under reduced pressure to give 207 mg of crude 5-[hydroxy-(3-propyl-pyrrolidin-3-yl)-methyl]-indazole-1-carboxylic acid tert-butyl ester as an off-white foam. This material was dissolved in toluene (8 mL) and activated manganese dioxide (85%, 240 mg, 2.80 mmol) was added. The resulting mixture was heated at 100° C. for 3 hours, then cooled to room temperature and filtered through a celite pad. The filtrate was evaporated under reduced pressure, and the resulting residue was purified by flash chromatography to give 86 mg of 5-(3-propyl-pyrrolidine-3-carbonyl)-indazole-1-carboxylic acid tert-butyl ester as a white foamy solid.

Provenance & Evidence