HCID 68508568, compound → HCID 23725954, compound

HRID 221930Notes

Reaction equation

HRID 221930 reaction equation
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@:10]21[C:50]1[CH:49]=[C:48]3[C:44]([CH:45]=[CH:46][N:47]3[CH2:51][C:52]3[CH:57]=[CH:56][C:55]([CH2:58][CH3:59])=[CH:54][CH:53]=3)=[CH:43][C:42]=1[CH2:41][O:40]2)C1C=CC=CC=1>CO.C1COCC1.[Pd]>[CH2:58]([C:55]1[CH:54]=[CH:53][C:52]([CH2:51][N:47]2[C:48]3[C:44](=[CH:43][C:42]4[CH2:41][O:40][C@@:10]5([C@H:9]([OH:8])[C@@H:14]([OH:15])[C@H:13]([OH:23])[C@@H:12]([CH2:31][OH:32])[O:11]5)[C:50]=4[CH:49]=3)[CH:45]=[CH:46]2)=[CH:57][CH:56]=1)[CH3:59]

Participants

5

Reactant 1

HCID 68508568HCID 68508568, compound

Product 1

HCID 23725954HCID 23725954, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3′R,4′S,5′S,6′R,7S)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-1-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-spiro[furo[3,4,f]indole-7(5H),2′-[2H]pyran] (43 mg, 0.055 mmol) in methanol (1 mL) and THF (1 mL) was added with 10% palladium on carbon (41 mg). The resultant solution was stirred under a hydrogen atmosphere for 1 hour at room temperature, and the catalyst was then filtered off. Solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solution=dichloromethane:methanol (10:1)), to thereby obtain the titled compound (10 mg, 43%).

Workup

  1. filtrationthe catalyst was then filtered off
  2. customSolvent was then removed by distillation under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (developing solution=dichloromethane:methanol (10:1))

Sources & evidence

ORD record
ord-dcaf5528e64e4fafb8df3c7e26a5485d
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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