Benzaldehyde → (2R)-2-(Benzylamino)propan-1-ol

HRID 2357638Notes

Reaction equation

HRID 2357638 reaction equation
[NH2:1][C@H:2]([CH3:5])[CH2:3][OH:4].[CH:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[BH4-].[Na+].CO>C1C=CC=CC=1>[CH2:6]([NH:1][C@H:2]([CH3:5])[CH2:3][OH:4])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 887MethanolHCID 80308(R)-(-)-2-Amino-1-propanolHCID 4311764Sodium borohydride

Product 1

HCID 7353896(2R)-2-(Benzylamino)propan-1-ol

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(R)-2-Aminopropan-1-ol (20.00 g, 266.3 mmol) was dissolved in benzene (266 mL) before benzaldehyde (26.91 mL, 266.3 mmol) was added and the reaction refluxed under a Dean-Stark trap for 1.5 h collecting 4.2 mL of water. The reaction mixture was cooled in an ice bath before sodium borohydride (10.07 g, 266.3 mmol) was added. The mixture was warmed to RT and stirred overnight. In an ice bath, methanol was added to the reaction mixture to quench the hydride, then the reaction concentrated, filtered, washed with dichloromethane, concentrated, and purified by flash chromatography to give the title compound. MS (ES+): 166 (M+H)+.

Workup

  1. additionwas added
  2. temperaturethe reaction refluxed under a Dean-Stark trap for 1.5 h
  3. customcollecting 4.2 mL of water
  4. additionwas added
  5. customto quench the hydride
  6. concentrationthe reaction concentrated
  7. filtrationfiltered
  8. washwashed with dichloromethane
  9. concentrationconcentrated
  10. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e4a01b71987647a88c0c9d35f487d506
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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