Borane → 3-Benzylamino-3-methyl-butan-1-ol

HRID 1244076Notes

Reaction equation

HRID 1244076 reaction equation
[CH2:1]([NH:8][C:9]([CH3:15])([CH3:14])[CH2:10][C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B>C1COCC1>[CH2:1]([NH:8][C:9]([CH3:15])([CH3:14])[CH2:10][CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 111382843-(Benzylamino)-3-methylbutanoic Acid

Product 1

HCID 219317683-Benzylamino-3-methyl-butan-1-olYield 47.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 3-Benzylamino-3-methyl-butyric acid (1.00 g, 4.83 mmol) in THF was added borane (9.7 mmol, 9.7 mL of a 1.0 M solution in THF). After stirring for 1 h, the mixture was quenched by pouring into a mixture of 1 M HCl and crushed ice. The mixture was neutralized with K2CO3 and extracted 1× with CHCl3. The material was dried via passage through cotton and concentrated to give 441 mg (47%) of the title compound: Rf 0.40 (12:88 MeOH/CHCl3).

Workup

  1. customthe mixture was quenched
  2. additionby pouring into a mixture of 1 M HCl
  3. customcrushed ice
  4. extractionextracted 1× with CHCl3
  5. customThe material was dried via passage through cotton
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f7f395e912394dbb9062091f22ecb6a2
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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