Tetrabutylammonium Fluoride → N,N-diethyl-2-(3-{(2R)-2-[(2 R)-2-hydroxy-2-(4-hydroxyphenyl) ethylamino]propyl}-1H-indol-7-yl-oxy)acetamide

Participants

Reaction Steps

A solution of 2-[3-((2R)-2-{2-[4-(tert-butyldimethylsilyloxy)-phenyl]-(2R)-2-(triethylsilyloxy)ethylamino}-propyl)-1H-indol-7-yloxy]-N,N-diethylacetamide (40 mg, 0.060 mmol) and TBAF (261 mg, 1 mmol) in tetrahydrofuran (1 mL) is stirred at room temperature for 8 hours. After concentrated, the resultant is purified by preparative TLC (thickness: 0.5 mm, methanol/(a saturated ammonia solution in chloroform)=1/10), extracted with saturated aqueous sodium hydrogen carbonate solution/chloroform. The organic layer is dried over sodium sulfate, and concentrated to give the desired N,N-diethyl-2-(3-{(2R)-2-[(2 R)-2-hydroxy-2-(4-hydroxyphenyl) ethylamino]propyl}-1H-indol-7-yl-oxy)acetamide (15 mg, yield: 55%).

Provenance & Evidence