HCID 131726204, compound → HCID 131726203, compound

HRID 1374306Notes

Reaction equation

HRID 1374306 reaction equation
[CH:1]([C@@H:4]1[CH2:9][CH:8]([N:10]([CH:12]([CH3:14])[CH3:13])[CH3:11])[CH2:7][CH2:6][C@@H:5]1[N:15]1[CH2:19][CH2:18][C@H:17]([NH:20]C(=O)OCC2C=CC=CC=2)[C:16]1=[O:31])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[NH2:20][C@H:17]1[CH2:18][CH2:19][N:15]([C@H:5]2[CH2:6][CH2:7][CH:8]([N:10]([CH:12]([CH3:13])[CH3:14])[CH3:11])[CH2:9][C@H:4]2[CH:1]([CH3:3])[CH3:2])[C:16]1=[O:31]

Participants

4

Reactant 1

HCID 131726204HCID 131726204, compound

Product 1

HCID 131726203HCID 131726203, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Benzyl (S)-1-((1S,2S,4R/S)-2-isopropyl-4-(isopropyl(methyl)amino)cyclohexyl)-2-oxopyrrolidin-3-ylcarbamate (160 mg) was dissolved in MeOH (6 mL) prior to the addition of 20% Pd(OH)2 (50 mg) in a Parr bottle. The bottle was evacuated and then back-filled with hydrogen; this was repeated three more times. The reaction was stirred under 60 psi of H2 for 5 h and then filtered and concentrated. The resulting residue was dissolved in MeOH (6 mL) prior to the addition of 20% Pd(OH)2 (75 mg) in a Parr bottle. The bottle was evacuated and then back-filled with hydrogen; this was repeated three more times. The reaction was stirred under 50 psi of H2 for 24 h and then filtered and concentrated to provide (S)-3-amino-1-((1S,2S,4R/S)-2-isopropyl-4-(isopropyl(methyl)amino)cyclohexyl)pyrrolidin-2-one (101 mg). MS (ES+)=296.3 (M+H)+.

Workup

  1. customThe bottle was evacuated
  2. additionback-filled with hydrogen
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe resulting residue was dissolved in MeOH (6 mL)
  6. additionto the addition of 20% Pd(OH)2 (75 mg) in a Parr bottle
  7. customThe bottle was evacuated
  8. additionback-filled with hydrogen
  9. stirringThe reaction was stirred under 50 psi of H2 for 24 h
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-7253cbd6debf4cb7a675bb43f8847e6b
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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