methyl(7S)-7-{2-[benzyl(methyl)amino]ethoxy}-14-cyclo hexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate → methyl (7S)-14-cyclohexyl-7-[2-(methylamino)ethoxy]-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 421952Notes

Reaction equation

HRID 421952 reaction equation
[CH2:1]([N:8](C)[CH2:9][CH2:10][O:11][C@H:12]1[CH2:19][N:18]2[C:20]3[CH:21]=[C:22]([C:33]([O:35][CH3:36])=[O:34])[CH:23]=[CH:24][C:25]=3[C:26]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[C:17]2[C:16]2[CH:37]=[CH:38][CH:39]=[CH:40][C:15]=2[O:14][CH2:13]1)C1C=CC=CC=1>CO.[Pd]>[CH:27]1([C:26]2[C:25]3[CH:24]=[CH:23][C:22]([C:33]([O:35][CH3:36])=[O:34])=[CH:21][C:20]=3[N:18]3[C:17]=2[C:16]2[CH:37]=[CH:38][CH:39]=[CH:40][C:15]=2[O:14][CH2:13][C@@H:12]([O:11][CH2:10][CH2:9][NH:8][CH3:1])[CH2:19]3)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 1

HCID 66674447methyl(7S)-7-{2-[benzyl(methyl)amino]ethoxy}-14-cyclo hexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 66674477methyl (7S)-14-cyclohexyl-7-[2-(methylamino)ethoxy]-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution (0.014 M) of methyl(7S)-7-{2-[benzyl(methyl)amino]ethoxy}-14-cyclo hexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate in anhydrous MeOH, Pd/C (1 eq.) was added and the resulting mixture was stirred for 12 h under an H2 atmosphere. The mixture was filtered and then concentrated in vacuo to afford the title compound. The product was used in the next step without further purification. (ES+) m/z 463 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c628b98c3ca40dea70abc1abbe32098
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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