Trifluoroacetic acid → 4-Isopropoxy-3-methylbenzaldehyde

Participants

Reaction Steps

To a solution of cis-8-ethoxy-10-(2-pyridyl)-11-oxa-3-azaspiro[5.5]undecane; 2,2,2-trifluoroacetic acid (42 mg, 0.11 mmol) in dichloromethane (1 mL) was added triethylamine (75 μL, 0.54 mmol). 4-isopropoxy-3-methyl-benzoyl chloride (46 mg, 0.21 mmol) (˜50% pure) was added. The mixture was stirred at rt for 15 min. Water was added. The aqueous layer was extracted with dichloromethane (2×). The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated to dryness. The crude material was purified by column chromatography (40-60% ethyl acetate-hex) to provide cis-8-ethoxy-10-(2-pyridyl)-11-oxa-3-azaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (37 mg). ESI-MS m/z calc. 452.27, found 453.3 (M+1)+; Retention time: 1.38 minutes (3 min run).

Provenance & Evidence