(Trifluoromethyl)trimethylsilane → HCID 57516616, compound

Participants

Reaction Conditions

Reaction Steps

In a 3-neck round-bottomed flask, benzyl 4-oxopiperidine-1-carboxylate (1.0 g, 4.3 mmol) was dissolved in THF (10 mL). The reaction mixture was cooled to 0° C. and trimethyl(trifluoromethyl)silane (0.78 mL, 5.3 mmol) was added. Then added TBAF (1.0M solution in THF, 0.05 mL, 0.05 mmol) which caused the internal temperature to rise to 30° C. The reaction mixture was stirred at room temperature overnight. Additional TBAF (1.0M solution in THF, 4.3 mL, 4.3 mmol) was added and the reaction mixture was stirred at room temperature for 4.25 h. The reaction mixture was quenched with water and extracted with CH2Cl2 (2×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The residue was triturated with toluene to afford 0.82 g (63%) of 4-hydroxy-4-trifluoromethyl-piperidine-1-carboxylic acid benzyl ester as a light yellow solid.

Provenance & Evidence