Hydrochloric Acid → HCID 24996754, compound

HRID 2076366Notes

Reaction equation

HRID 2076366 reaction equation
C([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]3[C:24]4[C:18]5([CH2:30][CH:21]([C:22](=[O:29])[C:23]=4[C:25]([F:28])([F:27])[F:26])[CH2:20][CH2:19]5)[CH2:17][C:14]=32)=[N:9]1)C1C=CC=CC=1.Cl.[H][H]>O1CCOCC1.[Pd]>[F:27][C:25]([F:26])([F:28])[C:23]1[C:22](=[O:29])[C@H:21]2[CH2:30][C@@:18]3([C:24]=1[C:13]1[CH:12]=[CH:11][C:10]4[NH:9][N:8]=[CH:16][C:15]=4[C:14]=1[CH2:17]3)[CH2:19][CH2:20]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 59397233HCID 59397233, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 24996754HCID 24996754, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-benzyl-6-(trifluoromethyl)-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one (0.820 g, 2.00 mmol) in 50 mL of dioxane was added 12N aqueous HCl (0.170 mL, 2.00 mmol) followed by 30% palladium on carbon (0.250 g) and the stirred mixture was hydrogenated under balloon pressure of hydrogen. After 45 minutes, additional 30% palladium on carbon (0.090 g) was added. After hydrogenating for an additional 1 hour, the mixture was filtered through a pad of silica gel, washing with EtOAc. The filtrate was washed with 5% aqueous NaHCO3 and the aqueous phase was back-extracted with EtOAc. The combined organic layers were diluted with Et2O and hexanes and washed with water and brine. The organic phase was concentrated under vacuum and the residue was chromatographed on silica gel (elution with 1:4 to 1:1 EtOAc/hexanes) to yield (rac)-(8R,10aS)-6-(trifluoromethyl)-3,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one as a white solid.

Workup

  1. waitAfter hydrogenating for an additional 1 hour
  2. filtrationthe mixture was filtered through a pad of silica gel
  3. washwashing with EtOAc
  4. washThe filtrate was washed with 5% aqueous NaHCO3
  5. extractionthe aqueous phase was back-extracted with EtOAc
  6. additionThe combined organic layers were diluted with Et2O and hexanes
  7. washwashed with water and brine
  8. concentrationThe organic phase was concentrated under vacuum
  9. customthe residue was chromatographed on silica gel (elution with 1:4 to 1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-9becce96733647de87d133627a9a7d52
Source dataset
uspto-grants-2011_04
Patent number
US07923568B2

Reaction notes

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