تفاعل #1333041

معادلة التفاعل

diisopropyl azodicarboxylate

1-tert-Butyloxycarbonyl-3-hydroxypyrrolidine

2-bromophenol

triphenylphosphine

→

title compound

المردود 44.0%

3-(2-Bromophenoxy)pyrrolidine

المردود 44.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated in vacuo
2. 2
   أخرىpartitioned between ether (50 ml) and water (50 ml)
3. 3
   استخلاصthe aqueous phase was extracted further with ether (50 ml)
4. 4
   غسيلThe combined organic phases were washed with water (2×25 ml), brine (2×25 ml)
5. 5
   تجفيفdried (MgSO4)
6. 6
   تركيزconcentrated in vacuo
7. 7
   workup.DISSOLUTIONThe product was dissolved in dichloromethane (10 ml)
8. 8
   workup.ADDITIONtrifluoroacetic acid (5 ml) was added
9. 9
   تركيزThe mixture was concentrated in vacuo
10. 10
    أخرىthe residue was purified by cation exchange chromatography
11. 11
    غسيلeluting with ammonia/methanol/dichloromethane mixtures

الإجراء التجريبي

1-tert-Butyloxycarbonyl-3-hydroxypyrrolidine (1 g), 2-bromophenol (710 mg) and triphenylphosphine (1.29 g) were dissolved in tetrahydrofuran (15 ml) and the mixture cooled in an ice bath before dropwise addition of diisopropyl azodicarboxylate (0.96 ml). The mixture was allowed to warm to room temperature over 3 h, concentrated in vacuo, partitioned between ether (50 ml) and water (50 ml) and the aqueous phase was extracted further with ether (50 ml). The combined organic phases were washed with water (2×25 ml), brine (2×25 ml), dried (MgSO4) and concentrated in vacuo. The product was dissolved in dichloromethane (10 ml) and trifluoroacetic acid (5 ml) was added and the reaction stirred for 1 h. The mixture was concentrated in vacuo and the residue was purified by cation exchange chromatography eluting with ammonia/methanol/dichloromethane mixtures. This gave the title compound as a pale orange oil (437 mg).

المصدر