Potassium Carbonate → HCID 86626239, compound

Participants

Reaction Steps

tert-Butyl 443-(1-methyl-1H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate and tert-Butyl 4-((3-(2-methyl-2H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate. tert-Butyl 4-((3-(1H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (80 mg, 0.15 mmol) methyl iodide (10.0 μL, 0.15 mmol) and potassium carbonate (21.0 mg, 0.15 mmol) were combined in acetone (1.5 mL) and heated at reflux overnight. After cooling to room temperature, the mixture was filtered and concentrated. Flash chromatography on silica gel (20% ethyl acetate/hexanes) afforded tert-Butyl 4-((3-(1-methyl-1H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (7.0 mg, 9%) and tert-Butyl 443-(2-methyl-2H-tetrazol-5-yl)-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (48 mg, 60%). Retention time: 4.75 min and 5.20 min. (Phenomenex C18 4.6×50 mm, 10% MeOH/90% H2O/0.1% TFA→90% MeOH/10% H2O/0.1% TFA, Gradient time=6 min., Flow rate=4 mL/min.): Mass spec.: 532.31 (MH)+ and 532.31 (MH)+ respectively.

Provenance & Evidence