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(6aR,7S,9aS,13aS)-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole → (6aR,7S,9aS,13aS)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-5-hydroxy-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

HRID 1417629
Notes
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Reaction equation

HRID 1417629 reaction equation
C([O:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:41])[C@@H:23]([CH3:40])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:39])([CH3:38])[C:28](=[N:31][N:32]5[CH2:37][CH2:36][O:35][CH2:34][CH2:33]5)[CH2:29][CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)C1C=CC=CC=1>CO.[C].[Pd]>[OH:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:41])[C@@H:23]([CH3:40])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:39])([CH3:38])[C:28](=[N:31][N:32]5[CH2:33][CH2:34][O:35][CH2:36][CH2:37]5)[CH2:29][CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 86753836(6aR,7S,9aS,13aS)-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

Product 1

HCID 86753837(6aR,7S,9aS,13aS)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-5-hydroxy-6a,7,10,10-tetramethyl-11-(1-oxa-4-azacyclohex-4-yl)imino-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindoleYield 81.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compound
Catalyst
HCID 887MethanolSolvent

Procedure

To a solution of Compound (61) (224 mg, 0.40 mmol) in 50 ml of methanol containing 1% water was added 180 mg of 10% palladium-carbon, followed by catalytic reduction. After the palladium-carbon was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel 10 g; ethyl acetate:methanol=99:1) and further crystallization from diethyl ether-n-hexane to give 152 mg (79%) of Compound (51f).

Workup

  1. customAfter the palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by a silica gel column chromatography (silica gel 10 g; ethyl acetate:methanol=99:1) and further crystallization from diethyl ether-n-hexane

Sources & evidence

ORD record
ord-21aaaf18b81c44468575da1faed23197
Source dataset
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05876984

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes