Tetrahydrofuran → 2-Aminobenzobicyclo[2.2.1]heptene

Temperature

0 °C

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.

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

ORD record

ord-738dc2c56bc1418393d37f88c7cbd95d

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05089506