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

HRID 1417631Notes

Reaction equation

HRID 1417631 reaction equation
C([O:8][C:9]1[C:10]2[CH2:29][C@:28]3([CH3:42])[C@@H:30]([CH3:41])[CH2:31][CH2:32][C@H:33]4[C:34]([CH3:40])([CH3:39])[C@@H:35]([OH:38])[CH2:36][CH2:37][C@@:27]34[O:26][C:11]=2[C:12]2[CH2:13][N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:15](=[O:18])[C:16]=2[CH:17]=1)C1C=CC=CC=1>CO.[C].[Pd]>[C:22]([O:21][C:19]([N:14]1[CH2:13][C:12]2[C:11]3[O:26][C@@:27]45[CH2:37][CH2:36][C@H:35]([OH:38])[C:34]([CH3:40])([CH3:39])[C@@H:33]4[CH2:32][CH2:31][C@H:30]([CH3:41])[C@@:28]5([CH3:42])[CH2:29][C:10]=3[C:9]([OH:8])=[CH:17][C:16]=2[C:15]1=[O:18])=[O:20])([CH3:24])([CH3:23])[CH3:25]

Participants

4

Reactant 1

HCID 86753807(6aR,7S,9aS,11S,13aS)-5-benzyloxy-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-11-hydroxy-6a,7, 10, 10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindole

Product 1

HCID 86753839(6aR,7S,9aS,11S,13aS)-2-(t-butoxycarbonyl)-2,3,6,6a,7,8,9,9a,10,11,12,13-dodecahydro-5,11-dihydroxy-6a,7,10,10-tetramethyl-3-oxo-1H-benzo[8,8a][1]benzopyrano[2,3-e]isoindoleYield 91%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of Compound (39a) (Step-1 in Example 44) (303 mg, 0.53 mmol) in 10 ml of methanol containing 1% water was added 30 mg of 10% palladium-carbon, followed by catalytic reduction under atomospheric pressure for 2.5 hours. After the catalyst was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by a column chromatography (silica gel 5 g; ethyl acetate) to give 234 mg (91%) of Compound (55a).

Workup

  1. customAfter the catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by a column chromatography (silica gel 5 g; ethyl acetate)

Sources & evidence

ORD record
ord-bdb7978f923540b9a5d02a364c865ced
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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