HCID 86596942, compound → HCID 69287214, compound

HRID 2225238Notes

Reaction equation

HRID 2225238 reaction equation
[CH:1](/[C@@H:5]1[CH2:10][C@H:9]([N:11]([CH:13]([CH3:15])[CH3:14])[CH3:12])[CH2:8][CH2:7][C@@H:6]1[NH:16]C(=O)OCC1C=CC=CC=1)=[CH:2]/[CH2:3][CH3:4]>CO.[OH-].[OH-].[Pd+2]>[CH2:1]([C@H:5]1[C@@H:6]([NH2:16])[CH2:7][CH2:8][C@@H:9]([N:11]([CH:13]([CH3:14])[CH3:15])[CH3:12])[CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 86596942HCID 86596942, compound

Product 1

HCID 69287214HCID 69287214, compoundYield 31.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A sample of benzyl (1S,2S,4R)-2-((Z)-but-1-enyl)-4-(isopropyl(methyl)amino)cyclohexylcarbamate (2.0 g, 5.6 mmol) was dissolved in MeOH (30 mL). The resulting solution was charged with Pearlman's catalyst (600 mg) and degassed under vacuum before being hydrogenated (50 psi H2) for 12 h. The mixture was filtered and concentrated in vacuo. The residue was dissolved in 30% HBr/AcOH (15 mL) and stirred for 30 min before being partitioned between Et2O and water. The aqueous phase was basified (NaOH) and extracted twice with EtOAc. The organic extracts were combined, dried (sodium sulfate), filtered, and concentrated to afford (1R,3R,4S)-3-butyl-N1-isopropyl-N1-methylcyclohexane-1,4-diamine (396 mg). MS found: (M+H)+=227.3.

Workup

  1. customdegassed under vacuum
  2. customfor 12 h
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in 30% HBr/AcOH (15 mL)
  6. custombefore being partitioned between Et2O and water
  7. extractionextracted twice with EtOAc
  8. dry with materialdried (sodium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f59e417878544a4e93cce0635fc5806f
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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