Ammonia methanol → (3S)-3-phenylcyclopentanamine

HRID 2404369Notes

Reaction equation

HRID 2404369 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][CH2:11][C:10](=[N:13]O)[CH2:9]2)=[CH:4][CH:3]=1.N.CO>[Ni].O>[C:5]1([C@H:8]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9]2)[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 21705897Ammonia methanolHCID 86671372(S)-3-(4-bromophenyl)cyclopentanone oxime

Product 1

HCID 68313398(3S)-3-phenylcyclopentanamineYield 92.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Procedure

A solution of Example 1C (10 g, 39.4 mmol) and 7M NH3/MeOH (100 mL) was added to Ra—Ni 2800, water slurry (40.0 g, 682 mmol) in a 50 mL pressure bottle. The mixture was stirred at room temperature for 32 hours at 30 psi. HPLC indicated complete reaction. The mixture was filtered through a nylon membrane, concentrated, and diluted with MTBE (300 mL) and 2N NaOH (150 mL). The layers were separated and the organic layer was washed with water (100 mL) and brine (50 mL), dried (Na2SO4), filtered, and concentrated to afford the title compound (5.86 g, 36.3 mmol, 92%). MS (LCMS) m/z 162 (M+H)+.

Workup

  1. customreaction
  2. filtrationThe mixture was filtered through a nylon membrane
  3. concentrationconcentrated
  4. additiondiluted with MTBE (300 mL) and 2N NaOH (150 mL)
  5. customThe layers were separated
  6. washthe organic layer was washed with water (100 mL) and brine (50 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-74c3611d2f2d4331b2f13943537956e8
Source dataset
uspto-grants-2014_08
Patent number
US08802711B2

Reaction notes

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