Tetrabutylammonium Fluoride → 4-(2-Cyclopropylindol-1-yl)cyclohexanol

Participants

Reaction Steps

Crude 1-[4-(tert-butyldimethylsilanyloxy)cyclohexyl]-2-cyclopropyl-1H-indole from above (10.4 mmol) was dissolved in tetrahydrofuran (150 mL), and tetrabutylammonium fluoride (21 mL, 1 M in THF, 21 mmol) was added. After the reaction was stirred for 72 hours it was concentrated and the residue partitioned between ethyl acetate and water. The organic layer was dried (MgSO4), concentrated and purified by SiO2 chromatography (10-50% ethyl acetate/hexanes) to give two (cis/trans) isomers (355 mg of the more polar isomer, 681 mg of the less polar isomer) of the desired alcohol. LC-MS (C17H21NO calc'd 255) m/z 256 (M+H).

Provenance & Evidence