Hydrochloric Acid → ethyl (4R)-4-[(8-bromo-9-methoxy-1,2,3,4-tetrahydrophenanthridin-6-yl)oxy]-L-prolinate hydrochloride
Reaction equation
[Br:1][C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:13]2[C:4](=[C:5]([O:18][C@H:19]3[CH2:23][N:22](C(OC(C)(C)C)=O)[C@H:21]([C:31]([OH:33])=[O:32])[CH2:20]3)[N:6]=[C:7]3[C:12]=2[CH2:11][CH2:10][CH2:9][CH2:8]3)[CH:3]=1.[ClH:34].[CH3:35][CH2:36]O>>[ClH:34].[Br:1][C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:13]2[C:4](=[C:5]([O:18][C@H:19]3[CH2:23][NH:22][C@H:21]([C:31]([O:33][CH2:35][CH3:36])=[O:32])[CH2:20]3)[N:6]=[C:7]3[C:12]=2[CH2:11][CH2:10][CH2:9][CH2:8]3)[CH:3]=1Participants
4
Procedure
To a solution of the product from Step 1, (4R)-4-[(8-bromo-9-methoxy-1,2,3,4-tetrahydrophenanthridin-6-yl)oxy]-1-(tert-butoxycarbonyl)-L-proline (500 mg, 0.96 mmol) in EtOH (80 mL) was bubbled HCl (g) for 30 min. The mixture was then stirred for 2 days at r.t. and then the solvent was removed in vacuo to yield the title compound. LRMS (M+H)+=448.9.