Potassium Carbonate → HCID 86635702, compound

Participants

Reaction Steps

Dimethyl 1-diazo-2-oxopropyl phosphonate (505 mg, 2627 μmol) (commercially available from TCI America Organic Chemicals Product List (Order Number D3546)), followed by K2CO3 (545 mg, 3941 μmol) was added to a diastereomeric mixture of (2R,5R)-tert-butyl 2-hydroxy-5-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyrrolidine-1-carboxylate and (2S,5R)-tert-butyl 2-hydroxy-5-((6-(trifluoromethyl)pyridin-3-yl)methyl)pyrrolidine-1-carboxylate (455 mg, 1314 μmol) in MeOH (1.3 mL) at room temperature. The mixture was stirred at room temperature for 4 hours, diluted with H2O (15 mL), and extracted with DCM (3×20 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting yellow solid was dissolved in MeOH/DCM, absorbed onto silica gel, and purified by flash chromatography (silica gel, 10% to 30% EtOAc/hexanes) to deliver (R)-tert-butyl 1-(6-(trifluoromethyl)pyridin-3-yl)hex-5-yn-2-ylcarbamate (284 mg, 63%) as an off-white solid. LCMS (API-ES) m/z: 343.1 (M+H+).

Provenance & Evidence