Tetrabutylammonium Fluoride → HCID 117653092, compound

Participants

Reaction Steps

To a solution of methyl 5-({(2S,5R)-1-(tert-butoxycarbonyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridine-2-carboxylate (475 mg, 0.88 mmol) in THF (2.0 mL) was added 1.0M solution of TBAF in THF (5 mL, 5.0 mmol) and the resulting solution stirred for an 30 minutes at room temperature. The mixture was concentrate under vacuum and the residue taken up in dichloromethane (50 mL). The solution was washed with water (50 mL) and brine (50 mL). The organics were then dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was purified vial preparative TLC plate (2×1000 μM) eluting with 80% ethyl acetate in hexane to afford the title compound as a white foam (334 mg, 89%). LC-MS: C24H30N2O5 calculated 426.24 found m/z (ES) 427.2 (MH)+ and 327.2 (M-Boc)+.

Provenance & Evidence