Ethyl N-methyl-N-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-glycinate → 1,1,1,3,3,3-Hexafluoro-2-{4-[(2-hydroxyethyl)(methyl)amino]phenyl}propan-2-ol

HRID 2184080Notes

Reaction equation

HRID 2184080 reaction equation
[CH3:1][N:2]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)[CH2:3][C:4](OCC)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:17][C:16]([F:18])([F:19])[C:15]([C:12]1[CH:13]=[CH:14][C:9]([N:2]([CH2:3][CH2:4][OH:5])[CH3:1])=[CH:10][CH:11]=1)([OH:24])[C:20]([F:21])([F:23])[F:22]

Participants

4

Reactant 2

HCID 10406140Ethyl N-methyl-N-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-glycinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 102452661,1,1,3,3,3-Hexafluoro-2-{4-[(2-hydroxyethyl)(methyl)amino]phenyl}propan-2-olYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl N-methyl-N-{4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-glycinate (272 mg, 0.76 mmol) was dissolved in anhydrous THF(5 mL) under argon and 1M lithium aluminum hydride solution in THF (1.1 mL, 1.1 mmol) was added. The resulting solution was stirred at ambient temperature over 18 h. The reaction was quenched slowly with ethyl acetate then diluted with H2O. The layers were separated and the organic phase was washed with water followed by brine. The organics were dried over MgSO4, filtered and concentrated in vacuo. The resultant oil was purified by flash chromatography (4:1 hexanes/EtOAc) to afford the title compound as a yellow oil (176 mg, 73%). 1H NMR (CDCl3) δ 7.56 (d, 2H), 6.86 (d, 2H), 3.86 (t, 2H), 3.55 (t, 2H), 3.06 (s, 3H). Anal. Calc. for C12H13NO2F6+0.1H2O: C, 45.18; H, 4.17; N, 4.39. Found: C, 45.01; H, 4.05; N, 4.28. HRMS (MH+) Calc.: 318.0918. Found: 318.0929.

Workup

  1. customThe reaction was quenched slowly with ethyl acetate
  2. additionthen diluted with H2O
  3. customThe layers were separated
  4. washthe organic phase was washed with water
  5. dry with materialThe organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resultant oil was purified by flash chromatography (4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-48f663a49ade4a799279a98e74447c4c
Source dataset
uspto-grants-2005_05
Patent number
US06900244B2

Reaction notes

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