HCID 178418361, compound → HCID 178460989, compound

HRID 1160257Notes

Reaction equation

HRID 1160257 reaction equation
C([O:8][C:9]1[CH:38]=[C:37]([Cl:39])[C:12]([CH2:13][C@@H:14]2[CH2:18][CH2:17][N:16]([C@H:19]3[CH2:24][CH2:23][C@H:22]([O:25][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])[CH2:21][CH2:20]3)[C:15]2=[O:36])=[C:11]([Cl:40])[CH:10]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[Cl:39][C:37]1[CH:38]=[C:9]([OH:8])[CH:10]=[C:11]([Cl:40])[C:12]=1[CH2:13][C@@H:14]1[CH2:18][CH2:17][N:16]([C@H:19]2[CH2:20][CH2:21][C@H:22]([O:25][Si:26]([CH:27]([CH3:28])[CH3:29])([CH:33]([CH3:34])[CH3:35])[CH:30]([CH3:31])[CH3:32])[CH2:23][CH2:24]2)[C:15]1=[O:36]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compound2×HCID 178460990HCID 178460990, compound

Product 1

HCID 178460989HCID 178460989, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Stir (R)-3-(4-Benzyloxy-2,6-dichloro-benzyl)-trans-1-(4-triisopropylsilanyloxy-cyclohexyl)-pyrrolidin-2-one (Preparation 17) (1.83 g, 3.03 mmol) and palladium hydroxide (20% on carbon) (0.200 g, 10% by weight) in 100 ml of Ethyl Acetate. Bubble hydrogen gas through the solution while stirring at room temperature for 5 minutes. Stir the mixture under the hydrogen gas atmosphere for 5 hours. Filter through celite and strip the solvent to receive 1.42 g of the title compound (91%). Mass spectrum (apci) m/z=514 (M+H).

Workup

  1. filtrationFilter through celite and strip the solvent

Sources & evidence

ORD record
ord-a604de1de2aa4e0ea8f1689e9b49fb07
Source dataset
uspto-grants-2010_10
Patent number
US07816349B2

Reaction notes

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