HCID 178418361, compound → HCID 178496578, compound

HRID 416003Notes

Reaction equation

HRID 416003 reaction equation
C([O:8][C:9]1[CH:29]=[C:28]([Cl:30])[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][CH3:26])[CH2:21][CH2:20]3)[C:15]2=[O:27])=[C:11]([Cl:31])[CH:10]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[Cl:31][C:11]1[CH:10]=[C:9]([OH:8])[CH:29]=[C:28]([Cl:30])[C:12]=1[CH2:13][C@@H:14]1[CH2:18][CH2:17][N:16]([C@H:19]2[CH2:24][CH2:23][C@H:22]([O:25][CH3:26])[CH2:21][CH2:20]2)[C:15]1=[O:27]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compound2×HCID 178496579HCID 178496579, compound

Product 1

HCID 178496578HCID 178496578, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Stir (R)-3-(4-benzyloxy-2,6-dichloro-benzyl)-trans-1-(4-methoxy-cyclohexyl)-pyrrolidin-2-one (2.59 g, 5.61 mmol) and palladium hydroxide (20% on carbon) (0.300 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 concentrate under vacuum to recover 2.08 g of the title compound (99%). MS (m/z): 372 (M+).

Workup

  1. filtrationFilter through Celite®
  2. concentrationconcentrate under vacuum
  3. customto recover 2.08 g of the title compound (99%)

Sources & evidence

ORD record
ord-91d5970fea8448f2a8b3c82c415c7ec7
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

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