Ethanol → HCID 86738231, compound

HRID 1106353Notes

Reaction equation

HRID 1106353 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:10]([N:12]1[CH2:17][CH2:16][C@H:15]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[C@H:14]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:13]1)=O)C.[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36].C(O)C>O1CCCC1.CCOCC>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36].[CH3:10][N:12]1[CH2:17][CH2:16][C@H:15]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[C@H:14]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:13]1

Participants

7

Reactant 4

HCID 702EthanolHCID 444972Fumaric AcidHCID 13039294HCID 13039294, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 86738231HCID 86738231, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 1.49 g of lithium aluminum hydride in 80 ml of anhydrous tetrahydrofuran is added, under nitrogen, a solution of 4.84 g of cis-1-ethoxycarbonyl-3-phenyl-4-(2-tolyloxy)piperidine. After 70 minutes at room temperature, the mixture is cooled, 80 ml of ether is added and the excess hydride is destroyed by the continuous addition of saturated sodium sulfate solution at 0°-10° C. until a flocculent white precipitate forms. The solid is filtered, washed with ether and the filtrate is concentrated in vacuo. The residue is partitioned between ether (200 ml) and water (100 ml). The ether phase is washed with saturated sodium chloride solution (100 ml), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a light yellow oil. The oil is dissolved in ether (50 ml) and treated with a solution of 1.77 g of fumaric acid in a mixture of ether (160 ml) and absolute ethanol (25 ml). After stirring overnight, the precipitate is filtered, washed with ether and dried to afford a colorless solid. Recrystallization from 90 ml of isopropanol affords product as a colorless solid, mp 169.5°-170.5° C. dec.

Workup

  1. additionis added, under nitrogen
  2. temperaturethe mixture is cooled
  3. customthe excess hydride is destroyed by the continuous addition of saturated sodium sulfate solution at 0°-10° C. until a flocculent white precipitate forms
  4. filtrationThe solid is filtered
  5. washwashed with ether
  6. concentrationthe filtrate is concentrated in vacuo
  7. customThe residue is partitioned between ether (200 ml) and water (100 ml)
  8. washThe ether phase is washed with saturated sodium chloride solution (100 ml)
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto afford a light yellow oil
  13. filtrationthe precipitate is filtered
  14. washwashed with ether
  15. customdried
  16. customto afford a colorless solid
  17. customRecrystallization from 90 ml of isopropanol
  18. customaffords product as a colorless solid, mp 169.5°-170.5° C. dec.

Sources & evidence

ORD record
ord-950fa29f2d9d42a9aab093d1bd727571
Source dataset
uspto-grants-1982_01
Patent number
US04312876

Reaction notes

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