反应详情

To a stirred solution of tert-butyl [1-(hydroxymethyl)tricyclo[3.3.1.03,7]non-3-yl]carbamate (0.65 g, 2.45 mmol) obtained in step VI in THF (10 mL) at ice bath temperature, was sequentially added Et3N (1.0 mL, 7.35 mmol), DMAP (20 mg, 0.16 mmol), and methanesulfonyl chloride (0.29 mL, 3.7 mmol). After stirring the reaction at the same temperature for 0.5 h, it was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography to obtain title compound {3-[(tert-butoxy carbonyl)amino]tricyclo[3.3.1.03,7]non-1-yl}methyl methane sulfonate as a viscous liquid (0.84 g) in 100% yield. m/z (M+1) 358; 1H NMR (CDCl3) 300 MHz δ 4.76 (s (br), 1H), 4.02 (s, 2H), 3.01 (s, 2H), 2.99 (s, 3H), 2.54-2.44 (m, 1H), 2.42-2.35 (m, 1H), 2.20-1.87 (m, 4H), 1.82 (dd, J=2.2, 10.5 Hz, 1H), 1.76-1.58 (m, 4H), 1.57-1.48 (m, 1H), 1.45 (s, 9H).

1. customthe reaction at the same temperature for 0.5 h
2. extractionextracted with EtOAc
3. washThe combined organic layers were washed with brine
4. dry with materialdried over Na2SO4
5. customthe solvent was removed under reduced pressure
6. customThe crude product was purified by column chromatography