Sodium borohydride → (S)-2-Amino-2-phenyl-1-propanol

HRID 605414Notes

Reaction equation

HRID 605414 reaction equation
[NH2:1][C@:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])[C:3](OCC)=[O:4].[BH4-].[Na+]>CCO>[NH2:1][C@:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:8])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86615568ethyl (2S)-2-amino-2-phenylpropanoate

Product 1

HCID 11205865(S)-2-Amino-2-phenyl-1-propanolYield 109.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product of Example 445C (1.28 g, 6.6 mmol, prepared in) was reacted with sodium borohydride (1.25 g, 33 mmol) in 75% aqueous EtOH (32 mL) at reflux for 1 hour. The reaction was concentrated, diluted with water (20 mL) and extracted with ethyl acetate (3×75 mL). The organic layer was washed with 10% NaHCO3 solution (2×10 mL), dried over MgSO4, and concentrated to give the title compound as colorless viscous oil (1.09 g., 100%).

Workup

  1. temperatureat reflux for 1 hour
  2. concentrationThe reaction was concentrated
  3. additiondiluted with water (20 mL)
  4. extractionextracted with ethyl acetate (3×75 mL)
  5. washThe organic layer was washed with 10% NaHCO3 solution (2×10 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c1b52354bd3a45acbc4422e3c866a469
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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