Water → HCID 54393263, compound

HRID 568785Notes

Reaction equation

HRID 568785 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH:7][CH2:8][C@@H:9]([NH:11][C:12](=O)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)[CH3:10].N(CCO)(CCO)CCO.O>C1COCC1>[CH3:23][O:22][C:16]1[CH:15]=[C:14]([CH2:13][CH2:12][NH:11][C@@H:9]([CH3:10])[CH2:8][OH:7])[CH:19]=[CH:18][C:17]=1[O:20][CH3:21]

Participants

6

Reactant 4

HCID 962Water2×HCID 7618TriethanolamineHCID 21226445Aluminium lithium hydride3×HCID 28345741HCID 28345741, compound

Product 1

HCID 54393263HCID 54393263, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 4 hr
  4. temperaturerefluxed another 3 hr
  5. temperaturethe reaction was refluxed overnight
  6. stirringthis was stirred overnight
  7. customThe solid that formed
  8. filtrationwas filtered off
  9. washthe filter cake was washed three times with ether
  10. washThe filtrate was washed with brine
  11. dry with materialdried (K2CO3)
  12. customThe solvent was removed in vacuo
  13. dissolutionThe residue was dissolved in ether/acetonitrile
  14. filtrationthe undissolved solid was filtered off
  15. customthe filtrate was evaporated in vacuo
  16. additionThe residue was treated with ethereal hydrogen chloride
  17. customthe solid was collected
  18. customThree recrystallizations from acetonitrile

Sources & evidence

ORD record
ord-4af54b206ba94be4851fb4ebd4b46def
Source dataset
uspto-grants-1988_03
Patent number
US04729994

Reaction notes

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