HCID 57545168, compound → HCID 11524939, compound

HRID 1661534Notes

Reaction equation

HRID 1661534 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:33]=[CH:32][C:10]2[C@:11]3([OH:31])[C@@H:16]([OH:17])[CH2:15][C@@H:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C@:12]3([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[O:13][C:9]=2[CH:8]=1)=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH2:4][CH2:5][O:6][C:7]1[CH:33]=[CH:32][C:10]2[C@:11]3([OH:31])[C@@H:16]([OH:17])[CH2:15][C@@H:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C@:12]3([C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)[O:13][C:9]=2[CH:8]=1

Participants

4

Reactant 1

HCID 57545168HCID 57545168, compound

Product 1

HCID 11524939HCID 11524939, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

210 mg (0.45 mmol) of (1S*,3S*,3aR*,8bS*)-6-(2-azidoethoxy)-3a-(4-chlorophenyl)-3-phenyl-2,3,3a,8b-tetrahydrocyclopenta[b]benzofuran-1,8b-(1H)-diol (Example 49A) are dissolved in 34 ml of ethanol. Addition of 56 mg of 10% palladium on activated carbon is followed by stirring at RT under hydrogen at atmospheric pressure for 15 minutes. The residue from filtration and concentration is filtered through silica gel 60. Toluene is used for washing, and a 1:1 dichloromethane/ethanol mixture is used for elution. Concentration results in 179 mg (90% of theory) of the product, which is finally purified by Method 23A.

Workup

  1. filtrationThe residue from filtration and concentration
  2. filtrationis filtered through silica gel 60
  3. washfor washing
  4. washa 1:1 dichloromethane/ethanol mixture is used for elution
  5. concentrationConcentration
  6. customresults in 179 mg (90% of theory) of the product, which
  7. customis finally purified by Method 23A

Sources & evidence

ORD record
ord-b5ddce79758e4e36ba9634798008d065
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

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