反应详情

温度

5 °C

Ethyl chloroformate (3.3 ml, 34 mmol) is added to a cooled (0° C.) solution of indan-2-yl acetic acid (5.0 g, 28.4 mmol) and triethylamine (4.75 ml, 34 mmol) in acetone (40 ml) and water (8 ml). After 30 minutes, a solution of sodium azide (2.8 g, 42.6 mmol) in water (16 ml) is added and the reaction is stirred at 5° C. for 1 hour, prior to addition of brine and ice. The mixture is extracted with ether and the combined extracts are dried (Na2SO4) and evaporated. The resultant acyl azide is taken into toluene (50 ml) and heated at 100° C. until nitrogen evolution ceases. After evaporation of solvent, the resultant isocyanate is taken into 6N HCl (40 ml) and heated at 100° C. for 16 hours. The reaction mixture is evaporated to ⅓ volume and the resultant solid collected by filtration, washed with water and ether, then dried. The resultant hydrochloride salt is suspended in ether (20 ml) and ammonia is bubbled for 10 minutes. Water is added and the organic layer is separated, dried (Na2SO4) and evaporated to afford the title compound [MH+CH3CN]+189.

1. extractionThe mixture is extracted with ether
2. dry with materialthe combined extracts are dried (Na2SO4)
3. customevaporated
4. temperatureheated at 100° C. until nitrogen evolution ceases
5. customAfter evaporation of solvent
6. temperatureheated at 100° C. for 16 hours
7. customThe reaction mixture is evaporated
8. filtrationthe resultant solid collected by filtration
9. washwashed with water and ether
10. customdried
11. customammonia is bubbled for 10 minutes
12. additionWater is added
13. customthe organic layer is separated
14. dry with materialdried (Na2SO4)
15. customevaporated