반응 #655967

반응 방정식

(S)-N-(2-hydroxy-1-methylethyl)-3,4-dimethoxybenzeneacetamide

triethanolamine

LAH

LAH

water

water

lithium aluminum hydride

→

(S)-2-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-1-propanol

수율 38.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   온도The reaction mixture was heated
3. 3
   온도under reflux for 4 hr
4. 4
   온도refluxed another 3 hr
5. 5
   온도the reaction was refluxed overnight
6. 6
   workup.STIRRINGthis was stirred overnight
7. 7
   기타The solid that formed
8. 8
   여과was filtered off
9. 9
   세척the filter cake was washed three times with ether
10. 10
    세척The filtrate was washed with brine
11. 11
    건조dried (K2CO3)
12. 12
    기타The solvent was removed in vacuo
13. 13
    workup.DISSOLUTIONThe residue was dissolved in ether/acetonitrile
14. 14
    여과the undissolved solid was filtered off
15. 15
    기타the filtrate was evaporated in vacuo
16. 16
    workup.ADDITIONThe residue was treated with ethereal hydrogen chloride
17. 17
    기타the solid was collected
18. 18
    기타Three recrystallizations from acetonitrile

실험 절차

To a suspension of 12.6 g (0.33 mole) lithium aluminum hydride (LAH) in 150 mL of dry THF under argon was added dropwise a suspension of 21.0 g (0.083 mole) (S)-N-(2-hydroxy-1-methylethyl)-3,4-dimethoxybenzeneacetamide in dry THF. The reaction mixture was heated under reflux for 4 hr. An additional 1.0 g of LAH was added and refluxed another 3 hr. An additional 3.0 g of LAH was added and the reaction was refluxed overnight. To the reaction was added 69 mL (0.48 mole) of triethanolamine over 1 hr. After stirring for 90 min, 16 ml of water was added and this was stirred overnight. An additional 12 ml of water was added. The solid that formed was filtered off and the filter cake was washed three times with ether and once with THF. The filtrate was washed with brine and dried (K2CO3). The solvent was removed in vacuo. The residue was dissolved in ether/acetonitrile, the undissolved solid was filtered off and the filtrate was evaporated in vacuo. The residue was treated with ethereal hydrogen chloride and the solid was collected. Three recrystallizations from acetonitrile gave 6.9 g of (S)-2-[[2-(3,4-dimethoxyphenyl)ethyl]amino]-1-propanol (38%) mp, 120°-123° C.

출처