反应详情

Reflux a mixture of the product of Step 1 (7.5 g, 17.5 mmol, 12/1 trans/cis mixture) and hydrazine hydrate (4.7 mL, 87.3 mmol) in CH3OH (40 mL) overnight, monitoring the reaction by TLC (30% EtOAc/hexanes) and adding additional hydrazine and refluxing further as necessary. Evaporate most of the solvent in vacuo and partition the resultant residue between water and EtOAc. Wash with water and brine, dry over Na2SO4 and concentrate onto silica gel to obtain a free-flowing powder. Load the powder onto a chromatography column packed with silica and EtOAc. Elute with EtOAc to obtain 3.8 g (50%) of the title compound as a 6/1 trans/cis mixture. 1H NMR (400 MHz, CDCl3, trans isomer) 7.74(2H, d, J=8.2 Hz), 7.39(2H, d, J=8.2 Hz), 7.28(2H, m), 7.16(5H, m), 6.76(2H, d, J=9.1 Hz), 4.63(1H, d, J=2.1 Hz), 3.73(3H, s), 3.06(1H, m), 2.65(2H, m), 1.98(1H, m), 1.85(3H, m). Diagnostic C-4 proton for cis diastereomer 5.16(J=5.6 Hz). MS(EI): 429(M+,74), 249(100), 149(35). HRMS calculated for C26H27N3O3 : 429.2052; found 429.2052.

1. temperatureReflux
2. temperaturerefluxing further as necessary
3. customEvaporate most of the solvent in vacuo
4. custompartition the resultant residue between water and EtOAc
5. washWash with water and brine
6. dry with materialdry over Na2SO4
7. concentrationconcentrate onto silica gel
8. customto obtain a free-flowing powder
9. washElute with EtOAc