Triethylamine → HCID 131723965, compound

Participants

Reaction Steps

To 3,7-di(tert-butoxycarbonyl)-3,7-diazabicyclononan-9-ol (475 mg, 1.39 mmol) in methylene chloride (25 mL) was added triethylamine (0.390 mL), 4-chlorobenzoyl chloride (0.23 mL, 1.81 mmol), and 4-dimethylaminopyridine (221 mg, 1.81 mmol). The reaction mixture was stirred for 2.5 h and was then diluted with methylene chloride and washed with 0.5N aqueous HCl and water. After drying over sodium sulfate the solution was concentrated and the residue was purified by column chromatography on silica gel with 25% ethyl acetate in hexanes to give the title compound (611 mg, 91%). 1H NMR (300 MHz, CDCl3) 1.18 (s, 18H), 1.80 (s, 3H), 3.00 (t, 2H), 3.31 (t, 2H), 3.99 (m, 3H), 4.30 (m, 2H); mass spectrum m/z 365 (M+Na)+.

Provenance & Evidence