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Acetic Acid → methyl (7S)-14-cyclohexyl-7-(pyrrolidin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 1669450
Notes
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Reaction equation

HRID 1669450 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C@H:15]1[CH2:22][N:21]2[C:23]3[CH:24]=[C:25]([C:36]([O:38][CH3:39])=[O:37])[CH:26]=[CH:27][C:28]=3[C:29]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[C:20]2[C:19]2[CH:40]=[CH:41][CH:42]=[CH:43][C:18]=2[O:17][CH2:16]1)C1C=CC=CC=1.CC(O)=O>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH:30]1([C:29]2[C:28]3[CH:27]=[CH:26][C:25]([C:36]([O:38][CH3:39])=[O:37])=[CH:24][C:23]=3[N:21]3[C:20]=2[C:19]2[CH:40]=[CH:41][CH:42]=[CH:43][C:18]=2[O:17][CH2:16][C@@H:15]([O:14][CH2:13][CH:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)[CH2:22]3)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67344945methyl (7S)-7-[(1-benzylpyrrolidin-2-yl)methoxy]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 67345272methyl (7S)-14-cyclohexyl-7-(pyrrolidin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylateYield 50%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxide
Catalyst
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl (7S)-7-[(1-benzylpyrrolidin-2-yl)methoxy]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.07 M) in EtOAc, was added an excess of AcOH (>50 eq) and Pd(OH)2/C. The atmosphere in the reaction flask was charged with H2 and the reaction stirred vigorously under a H2 atmosphere (balloon) at RT for 2 d. The mixture was filtered and the filtrate concentrated in vacuo. The crude was purified by FC (gradient from EtOAc/PE 6:4+1% NEt3 to EtOAc/PE 8:2+1% NEt3+5% MeOH) to afford the product (50%). (ES+) m/z 489 (M+H)+.

Workup

  1. additionThe atmosphere in the reaction flask was charged with H2
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe crude was purified by FC (gradient from EtOAc/PE 6:4+1% NEt3 to EtOAc/PE 8:2+1% NEt3+5% MeOH)

Sources & evidence

ORD record
ord-6fae9a1e43ca4bbe8b0b1d98f85da984
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07989438B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes