Nitrogen → HCID 68991151, compound

HRID 657154Notes

Reaction equation

HRID 657154 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C@H:13]1[CH2:18][C@@H:17]([O:19][CH3:20])[CH2:16][N:15](C(OCC2C=CC=CC=2)=O)[CH2:14]1.[H][H].N#N>CCO.[Pd]>[CH3:20][O:19][C@H:17]1[CH2:16][NH:15][CH2:14][C@@H:13]([CH2:12][N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]2=[O:1])[CH2:18]1

Participants

6

Reactant 3

HCID 947NitrogenHCID 131729316HCID 131729316, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68991151HCID 68991151, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To cis-phenylmethyl (3RS,5SR)-3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-5-(methyloxy)-1-piperidinecarboxylate (210 mg, 0.51 mmol) in EtOH (20 mL) was added Pd/C (50 mg; 10%). The reaction was hydrogenated on a Parr apparatus at 45 psi of H2 for 3 h. The hydrogen was displaced with N2 and the solution was filtered through a pad of Celite® to remove the catalyst which was washed with additional EtOH (50 mL). The filtrate was then concentrated under reduced pressure to give the desired compound (125 mg; 90%) as a colorless oil which was used without further purification.

Workup

  1. filtrationthe solution was filtered through a pad of Celite®
  2. customto remove the catalyst which
  3. washwas washed with additional EtOH (50 mL)
  4. concentrationThe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-9ba741437b5a4e24ab7a0e760b58fdbe
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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