Sodium borohydride → 2-(Benzylamino)-1-(4-methoxyphenyl)ethan-1-ol

HRID 397066Notes

Reaction equation

HRID 397066 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([NH:8][CH2:9][CH:10]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)[OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 16753664HCID 16753664, compound

Product 1

HCID 130729052-(Benzylamino)-1-(4-methoxyphenyl)ethan-1-olYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-benzylamino-1-(4-methoxy-phenyl)-ethanone (1.61 g, 6.30 mmol, see Preparation 60) in MeOH (60 ml) was added NaBH4 (0.48 g, 12.6 mmol) in three equal portions. The reaction was stirred at RT overnight, then it was quenched with a 1:1 mixture of water and sat. NaHCO3 (30 ml). The mixture was extracted with CH2Cl2 (3×40 ml), the organics were combined, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified via Biotage flash chromatography (SiO2, neat EtOAc) to give the title product (1.216 g, 4.72 mmol, 75% yield).

Workup

  1. customit was quenched with a 1:1 mixture of water and sat. NaHCO3 (30 ml)
  2. extractionThe mixture was extracted with CH2Cl2 (3×40 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified via Biotage flash chromatography (SiO2, neat EtOAc)

Sources & evidence

ORD record
ord-fd79b3cd26c641a2890b6bdf04fa1448
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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