Tetrabutylammonium Fluoride → Tert-butyl(2S,5R)-2-[(6-aminopyridin-3-yl)methyl]-5-[(R)-hydroxy(phenyl)methyl]pyrrolidine-1 carboxylate

Participants

Reaction Steps

To a solution tert-butyl(2S,5R)-2-[(6-aminopyridin-3-yl)methyl]-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate (40 mg, 0.08 mmol) in THF (0.5 mL) was added 1.0M solution of TBAF in THF (1 mL, 1.0 mmol) and the resulting solution stirred for an hour at room temperature. The mixture was concentrate under vacuum and the residue taken up in dichloromethane (10 mL). The solution was washed with water (5 mL) and brine (5 mL). The organics were then dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was purified vial preparative TLC plate (1000 μM) eluting with 5% methanol in dichloromethane to afford the title compound as a white foam (25.2 mg, 92%). LC-MS: C22H29N3O3 calculated 338.23 found m/z (ES) 339.2 (MH) and 239.2 (M-Boc)+.

Provenance & Evidence