Tetrahydrofuran → HCID 22346584, compound

HRID 398046Notes

Reaction equation

HRID 398046 reaction equation
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13])[C:3]([NH2:5])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[O-]S([O-])(=O)=O.[Na+].[Na+]>O>[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13])[CH2:3][NH2:5]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 22346608HCID 22346608, compound

Product 1

HCID 22346584HCID 22346584, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

2-Amino-3-(2-fluorophenyl)propionamide was added carefully to a chilled (5°) mixture of LAH (1.0 g, 26.3 mmol) and 20 ml THF under argon. The reaction was then heated at reflux for 10 hrs. The reaction was cooled to 5° C. and carefully treated with Na2SO4.10 H2O. The resulting mixture was stirred for 18 hrs, then filtered to remove the solids. The filtrate was concentrated in vacuo to give an amber oil. MS (m/z): 169 (M+H)+; C9H13FN2 requir. 168.19

Workup

  1. temperaturea chilled
  2. temperatureThe reaction was then heated
  3. temperatureat reflux for 10 hrs
  4. filtrationfiltered
  5. customto remove the solids
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto give an amber oil

Sources & evidence

ORD record
ord-29fe5172f9d94884869e0ed43b282c11
Source dataset
uspto-grants-2003_08
Patent number
US06610698B2

Reaction notes

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