HCID 86753797, compound → HCID 86753796, compound

HRID 1417604Notes

Reaction equation

HRID 1417604 reaction equation
C([O:8][C:9]1[C:10]2[CH2:21][C@:20]3([CH3:34])[C@@H:22]([CH3:33])[CH2:23][CH2:24][C@H:25]4[C:26]([CH3:32])([CH3:31])[C@@H:27]([OH:30])[CH2:28][CH2:29][C@@:19]34[O:18][C:11]=2[C:12]2[CH2:13][NH:14][CH2:15][C:16]=2[CH:17]=1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[OH:8][C:9]1[C:10]2[CH2:21][C@:20]3([CH3:34])[C@@H:22]([CH3:33])[CH2:23][CH2:24][C@H:25]4[C:26]([CH3:32])([CH3:31])[C@@H:27]([OH:30])[CH2:28][CH2:29][C@@:19]34[O:18][C:11]=2[C:12]2[CH2:13][NH:14][CH2:15][C:16]=2[CH:17]=1

Participants

4

Reactant 1

HCID 86753797HCID 86753797, compound

Product 1

HCID 86753796HCID 86753796, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To Compound (33a) (40 mg, 0.087 mmol) dissolved in 4.0 ml of ethanol was added 12 mg of 10% palladium-carbon, and the mixture stirred at room temperature for 2 hours under hydrogen atmosphere. After filtration for removing palladium-carbon, the reaction was concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (silica gel 2.0 g; chloroform:methanol:water=9:1:0.1-7:3:0.3). The fraction containing the desired compound was concentrated under reduced pressure. The residue was dissolved in a small amount of THF. To the solution was added ether gradually, and the precipitate formed was filtered to give Compound (34a) (17 mg, 53%) as a powder.

Workup

  1. filtrationAfter filtration
  2. customfor removing palladium-carbon
  3. concentrationthe reaction was concentrated under reduced pressure
  4. customThe residue was purified by a silica gel column chromatography (silica gel 2.0 g; chloroform:methanol:water=9:1:0.1-7:3:0.3)
  5. additionThe fraction containing the desired compound
  6. concentrationwas concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in a small amount of THF
  8. additionTo the solution was added ether gradually
  9. customthe precipitate formed
  10. filtrationwas filtered

Sources & evidence

ORD record
ord-d481dccc408b41ad8eb17c5d2831bfba
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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