Sodium → HCID 12327463, compound

HRID 2190296Notes

Reaction equation

HRID 2190296 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1[C:19]2[CH:18]([CH2:20][C:21]#[N:22])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1.[Na].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[K+]>C1COCC1>[CH:7]1[C:19]2[CH:18]([CH2:20][CH2:21][NH2:22])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 5360545SodiumHCID 6100505Dipotassium 2,3-dihydroxybutanedioateHCID 21226445Aluminium lithium hydrideHCID 57586376HCID 57586376, compound

Product 1

HCID 12327463HCID 12327463, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

6.3 mL (6.3 mmol, 2.7 eq) of a 1 M solution of LiAlH4 in THF were dissolved in 20 mL of THF in a 250 mL flask under argon. The reaction medium was cooled to −78° C. and 478 mg (2.3 mmol, 1 eq) of (9H-fluoren-9-yl)-acetonitrile in solution in 20 mL of THF were added dropwise. The temperature was allowed to rise progressively to ambient temperature. Stirring was continued for 5 hours, then the medium was hydrolysed at 0° C. by addition of 30 mL of a sodium and potassium tartrate solution. The THF was evaporated and the aqueous phase was extracted with ethyl acetate. After drying over MgSO4 and evaporation of the solvent, the crude product was subjected to chromatography over silica gel (elution gradient: CH2Cl2—CH2Cl2/MeOH: 9/1 to CH2Cl2/MeOH/NH4OH: 9/1/0.5). The 2-(9H-fluoren-9-yl)-ethylamine was obtained.

Workup

  1. customto rise progressively to ambient temperature
  2. customThe THF was evaporated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. dry with materialAfter drying over MgSO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-e1c8bd8f39734794bf7f3c0571662fbc
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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