Water → 2-[(4-Fluorophenyl)(2-hydroxyethyl)amino]ethan-1-ol

HRID 1282122Notes

Reaction equation

HRID 1282122 reaction equation
C([O:4][CH2:5][CH2:6][N:7]([CH2:15][C:16](OCC)=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)(=O)C.[BH4-].[Li+].O>O1CCCC1>[OH:4][CH2:5][CH2:6][N:7]([C:8]1[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=1)[CH2:15][CH2:16][OH:17]

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 57002313N-ethoxycarbonylmethyl-N-(4-fluorophenyl)-aminoethyl acetate

Product 1

HCID 184230372-[(4-Fluorophenyl)(2-hydroxyethyl)amino]ethan-1-olYield 96.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N-ethoxycarbonylmethyl-N-(4-fluorophenyl)-aminoethyl acetate (13.51 g) in tetrahydrofuran (135 ml) was added lithium borohydride (4.15 g) and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was poured into water (300 ml) and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the title compound (9.2 g) as a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c60eefab543941739e5c3ca386363e24
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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