Lithium aluminum hydride → (S)-2-Amino-2-(4-(trifluoromethyl)phenyl)ethanol

HRID 657764Notes

Reaction equation

HRID 657764 reaction equation
[AlH4-].[Li+].[CH:3]1[C:8]([C@H:9]([NH2:13])[C:10](O)=[O:11])=[CH:7][CH:6]=[C:5]([C:14]([F:17])([F:16])[F:15])[CH:4]=1>O1CCCC1>[NH2:13][C@@H:9]([C:8]1[CH:3]=[CH:4][C:5]([C:14]([F:15])([F:16])[F:17])=[CH:6][CH:7]=1)[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 28112Lithium aluminum hydrideHCID 14766374-(Trifluoromethyl)-L-phenylglycine

Product 1

HCID 10584357(S)-2-Amino-2-(4-(trifluoromethyl)phenyl)ethanolYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium tetrahydroaluminate (0.62 g, 0.016 mol) was added slowly, in small portions, to an ice cooled mixture of 4-(trifluoromethyl)-L-phenylglycine (1.8 g, 8.2 mmol) in tetrahydrofuran (60 mL). The mixture was slowly warmed to rt over a period of 1 h and then heated to reflux overnight. The solution was cooled to 0° C. and quenched with 2.0 M aqueous NaOH solution. The precipitate was filtered off and the filter cake was washed with THF. The filtrate was concentrated and extracted with CH2Cl2 (50 mL×3). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated in vacuo to give a light yellow solid (0.9 g, 59%). LC-MS: 206.2 [M+1]+.

Workup

  1. temperaturecooled
  2. temperatureheated
  3. temperatureto reflux overnight
  4. temperatureThe solution was cooled to 0° C.
  5. customquenched with 2.0 M aqueous NaOH solution
  6. filtrationThe precipitate was filtered off
  7. washthe filter cake was washed with THF
  8. concentrationThe filtrate was concentrated
  9. extractionextracted with CH2Cl2 (50 mL×3)
  10. washThe combined organic layers were washed with brine
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aacbc8f3942449b3a43cbaba451a9721
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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