(S)-4-Fluorophenylglycine → HCID 51669578, compound

HRID 2219882Notes

Reaction equation

HRID 2219882 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C@@H:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[C:9](O)=[O:10]>C1COCC1>[NH2:7][C@@H:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 853015(S)-4-FluorophenylglycineHCID 21226445Aluminium lithium hydride

Product 1

HCID 51669578HCID 51669578, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a 150 mL flame dry round bottom flask was added LiAlH4 (1.14 g, 29.9 mmol) and 70 mL THF. The solution was cooled to 0° C. and (S)-2-amino-2-(4-fluorophenyl)acetic acid (2.53 g, 15.0 mmol) was added portionwise. Following the addition, the reaction mixture was heated to reflux under N2 for 20 h. The resulting mixture was then cooled to 0° C. and quenched slowly with 5% NaHCO3. The solvents were removed and the residue was suspended in EtOAc. After 2 h, the white precipitate was filtered and the filtrate concentrated to give the title compound. MS (m/z): 156.3 (M+H) (Calc'd for C8H10FNO: 155.17).

Workup

  1. temperatureTo a 150 mL flame
  2. customdry round bottom flask
  3. additionthe addition
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux under N2 for 20 h
  6. temperatureThe resulting mixture was then cooled to 0° C.
  7. customquenched slowly with 5% NaHCO3
  8. customThe solvents were removed
  9. filtrationthe white precipitate was filtered
  10. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-f2768c71d10c43cc9209f0a0e0c176ad
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

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