Carbon Dioxide → Tert-butyl 2-(3-oxo-3-phenylpropyl)phenylcarbamate

HRID 1475909Notes

Reaction equation

HRID 1475909 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(=O)=O.[C:22]1([Li])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[O:1]=[C:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:11][CH2:10][C:9]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:3][C:12](=[O:13])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 25517Ammonium ChlorideHCID 10538446N-Boc-3,4-dihydro-2(1H)-quinolinoneHCID 178506676HCID 178506676, compound

Product 1

HCID 68281220Tert-butyl 2-(3-oxo-3-phenylpropyl)phenylcarbamateYield 78%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A reactor was charged with 2 mmol of tert-butyl 2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (ai1) obtained in Synthesis Example 1 and 6.9 mL of tetrahydrofuran as a solvent to prepare a solution. After cooling the solution to −78° C. using dry ice, 2.0 mL (1.1 M, 2.2 mmol) of phenyllithium (PhLi) was slowly added dropwise to the solution. The mixture was reacted at −78° C. for 7 hours with stirring. The mixture including the reaction product was added to an ammonium chloride aqueous solution (5 mL), and the mixture was stirred. The mixture was extracted twice with ethyl acetate, and the reaction product was washed with a sodium chloride solution. After the addition of excess anhydrous magnesium sulfate to the collected organic layer, the solvent was evaporated under reduced pressure to obtain a concentrate including a crude product. The concentrate was subjected to silica gel flash column chromatography (eluant: hexane/ethyl acetate=6/1) to obtain tert-butyl 2-(3-oxo-3-phenylpropyl)phenylcarbamate (white solid) represented by the following formula (an1) (yield: 78%). The analysis data for the resulting aniline derivative (an1) is shown below.

Workup

  1. customto prepare a solution
  2. additionwas slowly added dropwise to the solution
  3. customThe mixture was reacted at −78° C. for 7 hours
  4. stirringthe mixture was stirred
  5. extractionThe mixture was extracted twice with ethyl acetate
  6. washthe reaction product was washed with a sodium chloride solution
  7. additionAfter the addition of excess anhydrous magnesium sulfate to the collected organic layer
  8. customthe solvent was evaporated under reduced pressure
  9. customto obtain a concentrate

Sources & evidence

ORD record
ord-fc2ee0983d9d4867b641ca05588038de
Source dataset
uspto-grants-2015_04
Patent number
US09018394B2

Reaction notes

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