HCID 178455343, compound → HCID 178455342, compound

HRID 2235238Notes

Reaction equation

HRID 2235238 reaction equation
C([O:8][C:9]1[CH:35]=[C:34]([Cl:36])[C:12]([CH2:13][CH:14]2[CH2:18][CH2:17][N:16]([C@H:19]3[CH2:24][CH2:23][C@@H:22]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH2:21][CH2:20]3)[C:15]2=[O:33])=[C:11]([Cl:37])[CH:10]=1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].C1COCC1>[C:29]([Si:26]([CH3:28])([CH3:27])[O:25][C@@H:22]1[CH2:23][CH2:24][C@H:19]([N:16]2[CH2:17][CH2:18][CH:14]([CH2:13][C:12]3[C:11]([Cl:37])=[CH:10][C:9]([OH:8])=[CH:35][C:34]=3[Cl:36])[C:15]2=[O:33])[CH2:20][CH2:21]1)([CH3:31])([CH3:30])[CH3:32]

Participants

4

Reactant 1

HCID 178455343HCID 178455343, compound

Product 1

HCID 178455342HCID 178455342, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Combine 2 g (3.6 mmol) of 3-(4-benzyloxy-2,6-dichloro-benzyl)-1-[cis-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one (Preparation 71) with 150 mg Pd(OH)2 and 25 mL THF. Hydrogenate with a balloon of H2 for 3 hours. Filter the reaction through Celite®, concentrate under vacuum and purify by chromatography using CHCl3/MeOH 98/2 to recover 1.54 g (88%) of the title compound as an oil.

Workup

  1. filtrationFilter
  2. customthe reaction through Celite®
  3. concentrationconcentrate under vacuum
  4. custompurify by chromatography
  5. customto recover 1.54 g (88%) of the title compound as an oil

Sources & evidence

ORD record
ord-4ae46b1ce6bf4b528843db4ca53f1302
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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