Tetrabutylammonium Fluoride → HCID 59614360, compound

Participants

Reaction Steps

To a solution of (2S,3S,5R)-2-benzyl-3-(tert-butyl-dimethyl-silanyloxy)-5-ethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.243 mmol; 102 mg) in THF is added 1.0 M THF solution (0.36 mL) of tetra-n-butylammonium fluoride under nitrogen at room temperature. After 3 hours, The reaction mixture is quenched with saturated aqueous ammonium chloride solution, extracted three times with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtered, concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc) to give (2S,3S,5R)-2-benzyl-5-ethyl-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (74.4 mg, 99%); ESI-MS m/z: 250 [M+−tBu+2], Retention time 2.34 min (condition A).

Provenance & Evidence