Benzaldehyde → (R)(-)-2-Benzylamino-1-butanol

HRID 2367548Notes

Reaction equation

HRID 2367548 reaction equation
[NH2:1][C@H:2]([CH2:5][CH3:6])[CH2:3][OH:4].[CH:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[BH4-].[Na+].[OH-].[Na+]>CO>[C:8]1([CH2:7][NH:1][C@H:2]([CH2:5][CH3:6])[CH2:3][OH:4])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 27238562-Amino-1-butanol, (-)-HCID 4311764Sodium borohydride

Product 1

HCID 927306(R)(-)-2-Benzylamino-1-butanolYield 108.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (R)-(−)-2-amino-1-butanol (5 g, 56.1 mmol) in CH3OH (120 mL) was added benzaldehyde (6.24 mL, 61.7 mmol), and the reaction mixture was stirred under nitrogen for 15 minutes. The mixture was then cooled in an ice bath and sodium borohydride (2.33 g, 61.7 mmol) was added portionwise. The mixture was stirred in the ice bath for 1.5 hours. NaOH (6 N, 25 mL) was added and the mixture was concentrated. The resulting residue was taken up in 100 mL H2O and extracted with Et2O (2×). The organics were combined, dried over Na2SO4 and concentrated to afford the title compound (10.92 g) as a fluffy white solid. LC-MS (ES) m/z=180 [M+H]+.

Workup

  1. temperatureThe mixture was then cooled in an ice bath
  2. concentrationthe mixture was concentrated
  3. extractionextracted with Et2O (2×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7f20c51336c14bdd9cf8794cc468f408
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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