2-(Trifluoromethyl)benzylic alcohol → 2-(Trifluoromethyl)benzyl 7-bromo-3-oxo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

To o-(trifluoromethyl)benzyl alcohol (35 mg, 0.20 mmol) in CH2Cl2 (4 mL) was added was a solution of carbonyl diimidazole (29 mg, 0.18 mmol) in CH2Cl2 (4 mL). The mixture was stirred at rt for 2 h. A 1-mL aliquot of the resulting solution (0.05 mmol) was added to a solution 7-bromospiro[indene-1,4′-piperidin]-3(2H)-one (14.5 mg, 0.05 mmol) in CH2Cl2 (1 mL). The mixture was stirred at rt for 16 h, concentrated, redissolved in MeCN (1 mL) and heated at 60° C. for 2 h. Prep HPLC afforded the title compound. LC-MS Method 1 tR=2.06, min, m/z=484, 482.