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

HRID 1170017Notes

Reaction equation

HRID 1170017 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.C([O-])(O)=O.[Na+].[BH4-].[Na+]>CO>[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 80308(R)-(-)-2-Amino-1-propanolHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (2R)-2-amino propanol (1.2 equivalents), benzaldehyde (1 equivalent), NaHCO3 (1.5 equivalents), and MeOH, (˜1 M) was heated at reflux for 4 hours and then cooled to 0° C. Sodium borohydride (4.8 equivalents) was added portionwise to the stirred reaction mixture during a period of 2 hours at ca. 10° C. The whole was stirred at room temperature for 4 hours. The insoluble materials were filtered off and then the filtrate was concentrated to dryness. The residue was dissolved in CH2Cl2, and the solution was washed successively with water (2×) and brine (1×). The organic extracts were collected and dried (Na2SO4). The solvent was evaporated to give the desired product as a colorless oil, which solidified on standing and was used in the next step without further purification. GC/MS: 134 (100%, M+-CH2OH), Rt 11.57 minutes.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. filtrationThe insoluble materials were filtered off
  4. concentrationthe filtrate was concentrated to dryness
  5. dissolutionThe residue was dissolved in CH2Cl2
  6. washthe solution was washed successively with water (2×) and brine (1×)
  7. customThe organic extracts were collected
  8. dry with materialdried (Na2SO4)
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b3c07045a8d54e0b82fba5df785bb63d
Source dataset
uspto-grants-2010_11
Patent number
US07825132B2

Reaction notes

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