Borane;tetrahydrofuran → [1-(4-Nitrophenyl)cyclopropyl]methanamine

HRID 887623Notes

Reaction equation

HRID 887623 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:13]#[N:14])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].B.C1COCC1>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2([CH2:13][NH2:14])[CH2:11][CH2:12]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 43990411-(4-Nitrophenyl)cyclopropanecarbonitrile

Product 1

HCID 16641700[1-(4-Nitrophenyl)cyclopropyl]methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 1-(4-nitro-phenyl)-cyclopropanecarbonitrile (3.0 g, 15.9 mmol) and borane THF complex (1.0 M solution in THF, 32 ml, 32 mmol) in 50 ml of anhydrous THF was heated at reflux overnight. The mixture was cooled to RT, quenched with 2.5 ml of 50% AcOH aqueous solution, then partitioned between EtOAc and NaHCO3 (aq). The combined organic portions were washed with brine, dried with MgSO4, filtered, and condensed. The crude was purified by flash column chromatography (1 to 2% of MeOH in CH2Cl2). The titled compound was obtained as a light brownish solid. MS (ES+): 192.9. Calc'd for C10H12N2O2—192.2.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customquenched with 2.5 ml of 50% AcOH aqueous solution
  4. custompartitioned between EtOAc and NaHCO3 (aq)
  5. washThe combined organic portions were washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customcondensed
  9. customThe crude was purified by flash column chromatography (1 to 2% of MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-1e20907fe6064b8693e5e2463ef3dee3
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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