HCID 10103331, compound → 1478883-60-1

HRID 556831Notes

Reaction equation

HRID 556831 reaction equation
[CH3:1][N:2]1[C@H:7]2[CH2:8][CH2:9][C@@H:3]1[CH2:4][CH:5]([C:10]#[N:11])[CH2:6]2>N.CO.[Ni]>[CH3:1][N:2]1[C@H:7]2[CH2:8][CH2:9][C@@H:3]1[CH2:4][CH:5]([CH2:10][NH2:11])[CH2:6]2

Participants

4

Reactant 1

HCID 10103331HCID 10103331, compound

Product 1

HCID 517232761478883-60-1Yield 38%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

To a solution of (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octane-3-carbonitrile (J. Org. Chem., 1977, 3114) (83 mg, 0.55 mmol) in NH3/MeOH (0.5%) (10 mL) was added Raney Ni (ca. 50 mg). The reaction mixture was hydrogenated at atmospheric pressure for 16 hours. After filtration, the solvents were evaporated and the oil was purified by ion exchange on SCX-II acidic resin (2 g) eluting with methanol, then 2M ammonia-methanol. The basic fractions were combined and the solvent was removed in vacuo to give ((1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl)methanamine as colourless oil (32 mg, 38%).

Workup

  1. filtrationAfter filtration
  2. customthe solvents were evaporated
  3. customthe oil was purified by ion exchange on SCX-II acidic resin (2 g)
  4. washeluting with methanol
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-788673cdb603429b91592e27e35714d2
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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