Water → Methyl (1R,2S,3S,5S)-3-(4-bromophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate

関与物質

反応条件

反応手順

A mixture of 2β-Carbomethoxy-3β-(4′-trimethylsilylphenyl)tropane (594 mg, 1.79 mmol) and KBr (320 mg, 2.68 mmol) in 15 mL of acetic acid and 2 mL of MeOH was stirred at 60° C. for 20 min. 285 mg of NCS (2.15 mmol) was added at one time and the resulting mixture was stirred at the same temperature for 4 hrs. After cooling to rt 100 mL of H2O and 50 mL of Et2O were added. The aqueous phase was separated and the organic phase was extracted with 3N HCl (20 mL). The combined aqueous phase was washed with 20 mL of Et2O, basified with concentrated NH4OH and extracted with CH2Cl2 (2×50 mL). The solution was then dried and the removal of the solvent in vacuo gave the pure product as a white solid (607 mg, 100%). m.p. 114-116° C. 1H NMR (CDCl3, 400 MHz) δ 7.38 (d, J=8.4 Hz, 2H), 7.13 (d, J=8.4 Hz, 1H), 3.58-3.55 (m, 1H), 3.51 (s, 3H), 3.38-3.36 (m, 1H), 2.98-2.86 (m, 2H), 2.56 (dt, J−12.8, 2.8 Hz, 1H), 2.23 (s, 3H), 2.26.2.05 (m, 2H), 1.75-1.58 (m, 3H).

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