Triphenylphosphine → HCID 58993691, compound

Participants

Reaction Steps

tert-Butyl 4-phenyl-4-((3-(2,2,2-trifluoroacetamido)-5-(trifluoromethyl)benzyloxy)methyl)piperidine-1-carboxylate (100 mg, 0.18 mmol) in carbon tetrachloride (3 mL) was treated with triphenylphosphine (117 mg, 0.45 mmol) and heated at reflux overnight. After cooling to room temperature, the reaction was concentrated and the residue dissolved in dimethylformamide (2 mL). The mixture was treated with sodium azide (25 mg, 0.37 mmol) and stirred at room temperature for 5 h. The solvents were evaporated and the crude product purified by flash chromatography on silica gel (30% ethyl acetate/hexanes) to afford 46 mg (45%). 1H-NMR (CDCl3, 500 MHz) δ 7.61 (s, 1H), 7.59 (s, 1H), 7.30-7.32 (m, 2H), 7.23-7.26 (m, 2H), 7.12 (s, 1H), 7.05-7.08 (m, 1H), 4.51 (s, 2H), 3.74 (m, 2H), 3.46 (s, 2H), 2.99-3.03 (m, 2H), 2.21-2.24 (m, 2H), 1.79-1.84 (m, 2H), 1.42 (s, 9H). Mass spec.: 608.16 (MNa)+.

Provenance & Evidence