反应详情

A vigorously stirred solution of 1-benzhydryl-3-ethylaminoazetidine-3-carbonitrile (I-(13A-9)d; 11.7 g, 40 mmol) in methylene chloride (150 ml) cooled in an ice bath was treated with H2SO4 (22 ml, 0.4 mol), dropwise. After the reaction mixture was allowed to warm to room temperature and stir overnight, it was cooled in an ice bath and then carefully quenched with concentrated NH4OH to pH 11. The off-white solids that formed during the quench were collected by vacuum filtration. The aqueous mixture was then extracted with methylene chloride, the combined organic layers were washed with brine, dried (Na2SO4) and then concentrated, in vacuo, to afford additional solids. The combined solids were stirred for 1 hour in ethyl acetate (150 mL) and then collected by vacuum filtration to give I-(13A-9)e (9.2 g, 74%) as a solid: +ES MS (M+1) 310.2; 1H NMR (400 MHz, CD3OD) δ 7.41 (d, J=7.1 Hz, 4H), 7.25 (t, J=7.5 Hz, 4H), 7.16 (t, J=7.5 Hz, 2H), 4.49 (s, 1H), 3.44 (d, J=8.3 Hz, 2H), 3.11 (d, J=8.3 Hz, 2H), 2.47 (q, J=7.1 Hz, 2H), 1.10 (t, J=7.3 Hz, 3H).

1. temperatureit was cooled in an ice bath
2. customcarefully quenched with concentrated NH4OH to pH 11
3. customThe off-white solids that formed during the quench
4. filtrationwere collected by vacuum filtration
5. extractionThe aqueous mixture was then extracted with methylene chloride
6. washthe combined organic layers were washed with brine
7. dry with materialdried (Na2SO4)
8. concentrationconcentrated, in vacuo
9. customto afford additional solids
10. filtrationcollected by vacuum filtration
11. customto give I-(13A-9)e (9.2 g, 74%) as a solid