Diisobutylaluminum hydride → 2-methyl-2-(3-phenyl-1H-1,2,4-triazol-5-yl)propan-1-amine

HRID 1397324Notes

Reaction equation

HRID 1397324 reaction equation
CC(C[AlH]CC(C)C)C.[CH3:10][C:11]([C:15]1[NH:19][N:18]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:16]=1)([CH3:14])[C:12]#[N:13]>C1COCC1>[CH3:14][C:11]([C:15]1[NH:19][N:18]=[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:16]=1)([CH3:10])[CH2:12][NH2:13]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 67324319HCID 67324319, compound

Product 1

HCID 673242222-methyl-2-(3-phenyl-1H-1,2,4-triazol-5-yl)propan-1-amineYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIBAL-H (0.75 mL, 0.75 mmol, 1M in THF) was added to a solution of 2-methyl-2-(3-phenyl-1H-1,2,4-triazol-5-yl)propanenitrile (80 mg, 0.37 mmol) in dry THF (5 mL) at 0° C. The reaction mixture was allowed to warm up to room temperature and further stirred for 2 h. The reaction mixture was then quenched carefully with water and diluted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 2-methyl-2-(3-phenyl-1H-1,2,4-triazol-5-yl)propan-1-amine (70 mg, crude), which was carried through without further purification. MS (ESI) m/z: Calculated for C12H16N4: 216.14. found: 217.2 (M+H)+.

Workup

  1. customThe reaction mixture was then quenched carefully with water
  2. additiondiluted with EtOAc
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2eadf20b570648d984c1cf59c6d2d049
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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