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

HRID 1417618Notes

Reaction equation

HRID 1417618 reaction equation
[NH2:1][C@@H:2]1[C:31]([CH3:33])([CH3:32])[C@H:30]2[C@@:5]3([O:26][C:9]4[C:10]5[CH2:11][NH:12][C:13](=[O:25])[C:14]=5[CH:15]=[C:16]([O:17]CC5C=CC=CC=5)[C:8]=4[CH2:7][C@:6]3([CH3:35])[C@@H:27]([CH3:34])[CH2:28][CH2:29]2)[CH2:4][CH2:3]1>CO.[C].[Pd]>[NH2:1][C@@H:2]1[C:31]([CH3:33])([CH3:32])[C@H:30]2[C@@:5]3([O:26][C:9]4[C:10]5[CH2:11][NH:12][C:13](=[O:25])[C:14]=5[CH:15]=[C:16]([OH:17])[C:8]=4[CH2:7][C@:6]3([CH3:35])[C@@H:27]([CH3:34])[CH2:28][CH2:29]2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 86753817(6aR,7S,9aS,11S,13aS)-11-amino-5-benzyloxy-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

Product 1

HCID 86753818(6aR,7S,9aS,11S,13aS)-11-amino-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-5-hydroxy-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindoleYield 66%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To Compound (46a) (30 mg, 0.063 mmol) dissolved in 4.0 ml of methanol was added 6 mg of 10% palladium-carbon, and the mixture stirred under hydrogen atmosphere for 1 hour at room temperature. After the palladium-carbon was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was crystallized from diethyl ether, and recrystallized from diethyl ether-methanol to give 16 mg (48%) of Compound (47a).

Workup

  1. customAfter the palladium-carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was crystallized from diethyl ether
  4. customrecrystallized from diethyl ether-methanol

Sources & evidence

ORD record
ord-4d9b3d0489af427ab925535da3167757
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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