HCID 178418361, compound → HCID 178516680, compound

HRID 1013797Notes

Reaction equation

HRID 1013797 reaction equation
C([O:8][C:9]1[CH:30]=[C:29]([Cl:31])[C:12]([CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16]([C@H:19]3[CH2:27][CH2:26][C:25]4[C:21](=[CH:22][NH:23][N:24]=4)[CH2:20]3)[C:15]2=[O:28])=[C:11]([Cl:32])[CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][C:9]1[CH:30]=[C:29]([Cl:31])[C:12]([CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16]([C@H:19]3[CH2:27][CH2:26][C:25]4[C:21](=[CH:22][NH:23][N:24]=4)[CH2:20]3)[C:15]2=[O:28])=[C:11]([Cl:32])[CH:10]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178516681HCID 178516681, compound

Product 1

HCID 178516680HCID 178516680, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Dissolve (3R,5S)-3-(4-Benzyloxy-2,6-dichloro-benzyl)-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one (Example 35) (8.79 g, 18.7 mmol) in absolute ethanol (60 mL), treat with 20% Pd(OH)2 (6.0 g) and stir at 30 psi hydrogen pressure. After 6 h, ESMS shows starting material consumed and product formed. Remove the catalyst by filtration, rinse with ethanol and evaporate to a dark foam. Filtration through 50 g SCX mega-bond elut using 95:5 CH2Cl2/MeOH followed by 95:5 CH2Cl2/7.0 M NH3/MeOH yields 5.6 g (79%) as an amorphous solid MS (m/z): 380 (M+1)

Workup

  1. customconsumed
  2. customproduct formed
  3. customRemove the catalyst
  4. filtrationby filtration
  5. washrinse with ethanol
  6. customevaporate to a dark foam
  7. filtrationFiltration through 50 g SCX mega-bond elut
  8. customyields 5.6 g (79%) as an amorphous solid MS (m/z)

Sources & evidence

ORD record
ord-4b332b8ed8134437a345fe3ddc410ebb
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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