Water → 2-(2,6-Dimethoxyphenyl)-2-((4-(trifluoromethoxy)benzyl)-amino)ethanol

HRID 594416Notes

Reaction equation

HRID 594416 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[CH:17]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=1)[C:18](OCC)=[O:19].O.[OH-].[Na+]>C1COCC1>[CH3:16][O:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH3:7])[C:10]=1[CH:17]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]([F:33])([F:35])[F:34])=[CH:27][CH:26]=1)[CH2:18][OH:19]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69080982Ethyl 2-(2,6-dimethoxyphenyl)-2-((4-(trifluoromethoxy)benzyl)amino)acetate

Product 1

HCID 690857062-(2,6-Dimethoxyphenyl)-2-((4-(trifluoromethoxy)benzyl)-amino)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled (0° C.) mixture of LiAlH4 (6 mg; 0.15 mmol) in anh. THF (1 ml) was treated dropwise with a solution of ethyl 2-(2,6-dimethoxyphenyl)-2-((4-(trifluoromethoxy)benzyl)amino)acetate (65 mg; 0.15 mmol) in anh. THF (1 ml). The resulting mixture was further stirred at rt, under nitrogen, for 1 h. Water (6 μl), 15% aq. NaOH (6 μl), and water (18 μl) were then successively added, and the heterogeneous mixture was filtered. The filtrate was concentrated to dryness under reduced pressure, and the oily residue was further dried under HV affording 2-(2,6-dimethoxyphenyl)-2-((4-(trifluoromethoxy)benzyl)-amino)ethanol as a yellow oil. LC-MS (conditions E): tR=0.59 min.; [M+H]+: 372.10 g/mol.

Workup

  1. temperatureA cooled
  2. filtrationthe heterogeneous mixture was filtered
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. customthe oily residue was further dried under HV

Sources & evidence

ORD record
ord-a1ab625b240d49d8b6ebf059484ea775
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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