Hydrochloric Acid → 5,6,7,8,9,10-Hexahydro-2-methyl-5,9-methanopyrido[4,3-d]azocin-1(2H)-one
Reaction equation
C(OC([N:8]1[CH2:19][CH:18]2[CH2:20][CH:10]([CH2:11][C:12]3[C:13](=[O:22])[N:14]([CH3:21])[CH:15]=[CH:16][C:17]=32)[CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[CH3:21][N:14]1[C:13](=[O:22])[C:12]2[CH2:11][CH:10]3[CH2:20][CH:18]([CH2:19][NH:8][CH2:9]3)[C:17]=2[CH:16]=[CH:15]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 5-methyl-6-oxo-5,11-diaza-tricyclo[7.3.1.02,7]trideca-2(7),3-diene-11-carboxylic acid tert-butylester (22 mg, 0.07 mmol) (prepared above) was added anhydrous 3N HCl in ethyl acetate and the solution was stirred at room temperature for 16 h. The reaction mixture was evaporated in vacuo and the resulting white solid was recrystallized from methanol-ether to afford the desired product (9 mg, 64%). 1H NMR (CD3OD, 400 MHz) δ 7.53 (d, 1H, J=7 Hz), 6.25 (d, 1H, J=7 Hz), 3.54 (s, 3H), 3.3 (obsc. M, 4H), 3.08 (br.s, 1H), 2.85 (dd, 1H, J=19 Hz, J=7 Hz), 2.65 (d, 1H, J=19 Hz), 2.55 (br.s, 1H), 2.08 (d, 1H, J=13 Hz), 1.89 (d, 1H, J=13 Hz); APCl MS m/z 205 (M+1)+.