Sodium Sulfate → HCID 86738229, compound

HRID 851056Notes

Reaction equation

HRID 851056 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([C:10]([N:12]2[CH2:17][CH2:16][C@@H:15]([O:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C@H:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:13]2)=O)[CH2:9][CH2:8]1.S([O-])([O-])(=O)=O.[Na+].[Na+].[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43]>O1CCCC1.CO.CC(C)=O.CCOCC.C(O)C>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43].[CH:7]1([CH2:10][N:12]2[CH2:17][CH2:16][C@@H:15]([O:18][C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[C@H:14]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:13]2)[CH2:8][CH2:9]1

Participants

9

Reactant 4

HCID 24436Sodium SulfateHCID 444972Fumaric AcidHCID 13039273HCID 13039273, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 86738229HCID 86738229, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent3×HCID 8028TetrahydrofuranSolvent2×HCID 21894497Aceton-methanolSolvent

Procedure

To a suspension of 0.79 g of lithium aluminum hydride in 60 ml of anhydrous tetrahydrofuran is added, dropwise at room temperature under nitrogen, a solution of 3.53 g of trans-1-cyclopropylcarbonyl-4-(4-fluorophenoxy)-3-phenylpiperidine in 60 ml of tetrahydrofuran. After the addition is complete the mixture is stirred at room temperature for 2 hours and cooled in ice/isopropanol to -5° C. Ether is added (60 ml), followed by cautious, dropwise addition of saturated sodium sulfate solution. The flocculent white precipitate thus obtained is filtered and washed well with ether. The filtrate is concentrated in vacuo. The residue is dissolved in ether (200 ml) and the solution is washed with saturated sodium chloride solution (100 ml), dried overnight over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a nearly colorless oil. The oil is dissolved in 25% methanol/acetone solution and passed through a small silica gel column. The resulting oil is dissolved in ether (50 ml) and treated dropwise with a solution of 0.98 g of fumaric acid in a mixture of ether (60 ml) and absolute ethanol (15 ml) and the resulting mixture is stirred at room temperature overnight. The salt is filtered, washed with ether and dried to afford product as colorless solid, mp 185.5°-187° C. dec.

Workup

  1. additionis added, dropwise at room temperature under nitrogen
  2. additionAfter the addition
  3. customThe flocculent white precipitate thus obtained
  4. filtrationis filtered
  5. washwashed well with ether
  6. concentrationThe filtrate is concentrated in vacuo
  7. dissolutionThe residue is dissolved in ether (200 ml)
  8. washthe solution is washed with saturated sodium chloride solution (100 ml)
  9. dry with materialdried overnight over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto afford a nearly colorless oil
  13. stirringthe resulting mixture is stirred at room temperature overnight
  14. filtrationThe salt is filtered
  15. washwashed with ether
  16. customdried
  17. customto afford product as colorless solid, mp 185.5°-187° C. dec.

Sources & evidence

ORD record
ord-8bfb6c5799c14ccf895cc24c0926dc05
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

Loading…