Borane;tetrahydrofuran → 3-Aminomethyl-6-(iso-propoxy)methyl-pyridine

HRID 1190974Notes

Reaction equation

HRID 1190974 reaction equation
B.C1COCC1.[CH:7]([O:10][CH2:11][C:12]1[N:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1)([CH3:9])[CH3:8]>Cl>[NH2:19][CH2:18][C:15]1[CH:16]=[N:17][C:12]([CH2:11][O:10][CH:7]([CH3:9])[CH3:8])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 584956066-(Iso-propoxy)methyl-pyridine-3-carbonitrile

Product 1

HCID 584955003-Aminomethyl-6-(iso-propoxy)methyl-pyridineYield 46.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Add a solution of borane-THF complex (4.5 mL, 4.54 mmol, 1M solution in THF) to neat 6-(iso-propoxy)methyl-pyridine-3-carbonitrile (0.4 g, 2.27 mmol) and stir the mixture for 16 h at reflux. Cool to room temperature and stir for 48 h. Add 2N aqueous HCl (10 mL) until gas evolution stops and then concentrate in vacuo. Dissolve the crude mixture in methanol and filter through a SCX-2 column eluting with methanol followed by 3N ammonia in methanol to obtain the title compound (190 mg, 46%).

Workup

  1. temperatureat reflux
  2. stirringstir for 48 h
  3. concentrationconcentrate in vacuo
  4. dissolutionDissolve the crude mixture in methanol
  5. filtrationfilter through a SCX-2 column
  6. washeluting with methanol

Sources & evidence

ORD record
ord-cdbb2bbeef9b4678b88ab5310ebb326e
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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