Lithium Bromide → 2-[(3-Methoxyphenyl)methylamino]ethanol

HRID 85307Notes

Reaction equation

HRID 85307 reaction equation
[BH4-].[Na+].[Li+].[Br-].C([O:7][C:8](=O)[CH2:9][NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)C>C1COCC1>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([CH2:11][NH:10][CH2:9][CH2:8][OH:7])[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 82050Lithium BromideHCID 4311764Sodium borohydrideHCID 12867068N-((3-Methoxyphenyl)methyl)glycine ethyl ester

Product 1

HCID 47172572-[(3-Methoxyphenyl)methylamino]ethanolYield 135%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
80 °C

Procedure

Next, NaBH4 (3.8 g, 100 mmol) and LiBr (8.7 g, 100 mmol) were added to THF (100 ml), and the mixture was stirred at 80° C. for 1 hour. To this mixture, [(3-methoxyphenyl)methylamino]acetic acid ethyl ester (7.4 g, 33.1 mmol) dissolved in THF (20 ml) was added dropwise at room temperature. The mixture was stirred at 80° C. for 5 hours and further at room temperature for 16 hours. After the reaction solvent was evaporated to about half, KH2PO4 (1 M, 200 ml) was slowly added dropwise thereto. The organic layer was extracted with dichloromethane (50 ml) times and dried over Na2SO4 to give crude 2-[(3-methoxyphenyl)methylamino]ethanol (yield: 8.1 g).

Workup

  1. additionwas added dropwise at room temperature
  2. stirringThe mixture was stirred at 80° C. for 5 hours and further at room temperature for 16 hours
  3. customAfter the reaction solvent was evaporated to about half, KH2PO4 (1 M, 200 ml)
  4. additionwas slowly added dropwise
  5. extractionThe organic layer was extracted with dichloromethane (50 ml) times
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-2e70cc22a940422ab8e1a922df0930ea
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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