Tetrahydrofuran → 2-Aminobenzobicyclo[2.2.1]heptene

HRID 1534431Notes

Reaction equation

HRID 1534431 reaction equation
[N-:1]=[N+]=[N-].[Na+].O1CCCC1.[C:10]12[CH2:16][C:13](=[CH:14][CH:15]=1)[C:12]1[CH:17]=[CH:18][CH:19]=[CH:20][C:11]2=1.[OH-].[Na+]>O.[BH4-].[Na+]>[NH2:1][C:15]1[CH:14]=[C:13]2[CH2:16][C:10]=1[C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]2=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 566125711,4-Methanonaphthalene

Product 1

HCID 214136102-Aminobenzobicyclo[2.2.1]heptene

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 4311764Sodium borohydrideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium azide (2 g) was combined with water (40 ml) and tetrahydrofuran (40 ml) and cooled to 0° C. Mercuric acetate (4g) was added to the cold solution and the mixture was stirred for 20 minutes. Benzobicyclo[2.2.1]heptadiene (2 g) was added to the stirred mixture and the resulting mixture was heated to 75° C. for 24 hours. The solution was cooled to room temperature, treated with 10% sodium hydroxide in water (10 ml) and sodium borohydride (0.4 g), and stirred for 1 hour. The two layers were separated and the organic layer was dried over magnesium sulfate and the solvent removed on a rotary evaporator. The residue was combined with tetrahydrofuran (20 ml) and added to a suspension of lithium aluminum hydride (0.1 g) in tetrahydrofuran (20 ml). The mixture was stirred at room temperature for 3 hours, treated with water (1 ml) and filtered. The solvent was removed on a rotary evaporator to provide the product as a yellow oil.

Workup

  1. temperaturethe resulting mixture was heated to 75° C. for 24 hours
  2. temperatureThe solution was cooled to room temperature
  3. stirringstirred for 1 hour
  4. customThe two layers were separated
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. customthe solvent removed on a rotary evaporator
  7. additionadded to a suspension of lithium aluminum hydride (0.1 g) in tetrahydrofuran (20 ml)
  8. stirringThe mixture was stirred at room temperature for 3 hours
  9. additiontreated with water (1 ml)
  10. filtrationfiltered
  11. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-738dc2c56bc1418393d37f88c7cbd95d
Source dataset
uspto-grants-1992_02
Patent number
US05089506

Reaction notes

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