Potassium tert-butoxide → HCID 70197161, compound

Participants

Reaction Conditions

Reaction Steps

Epimerization of the cis isomer to the trans isomer was accomplished by adding potassium t-butoxide (75 mg, 0.67 mmol) to a solution of cis-N-(2,3,4,5-tetrahydro-2-oxo-1-methyl-5-phenyl-1H-benzazepin-3-yl)-3-cyclohexylpropanamide (90 mg, 0.22 mmol) in tetrahydrofuran (10 ml) and heating to 50° C. for 18 hours. The mixture was diluted with ethyl acetate (50 ml) and saturated aqueous sodium hydrogen carbonate (100 ml). The organic layer was separated and the aqueous layer was extracted again with ethyl acetate (2×40 ml). The organic layers were combined and concentrated at reduced pressure. The resulting mixture of isomers was crystallized from a mixture of ethyl acetate and hexane, from which was obtained the desired trans isomer (35 mg, 39%). m.p. 185°-186° C. 1H NMR 8 7.40-7.09 (m, 8H), 6.74 (d, J=8.4 Hz, 1H), 6.61 (d, J=6.6 Hz, 1H), 4.60-4.50 (m, 1H), 4.32-4.22 (m, 1H), 3.51 (s, 3H), 3.33-3.10 (m, 1H), 2.21 (t, J=7.8 Hz, 2H), 2.15-2.02 (m, 1H), 1.76-1.44 (m, 5H), 1.30-1.15 (m, 4H), 0.96-0.80 (m, 2H). Anal. Calcd. for C26H32N2O2.H2O: C, 76.01; H, 8.02; N, 6.82. Found: C, 76.00; H, 7.75; N, 6.91%.

Provenance & Evidence