Hydrochloric Acid → HCID 13039300, compound

HRID 851067Notes

Reaction equation

HRID 851067 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9]1)=[O:7])[CH3:4].[Cl-].[Na+].Cl>C(O)C>[CH2:3]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([OH:14])[C@H:10]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:9]1)=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 20503534HCID 20503534, compound

Product 1

HCID 13039300HCID 13039300, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 7.34 g of sodium borohydride in 315 ml of denatured ethanol is added, dropwise with stirring under nitrogen over a 30-minute period, a solution of 48.0 g of 1-ethoxycarbonyl-3-phenyl-4-piperidone in 485 ml of denatured ethanol, keeping the temperature below 10° C. during the addition. After stirring overnight at room temperature, 1200 ml of saturated sodium chloride is added. After stirring for one hour 500 ml of 2 N hydrochloric acid is cautiously added. The mixture is extracted with ether (3×600 ml). The solvent is removed in vacuo from the organic extracts and the residue is partitioned between ether (1200 ml) and saturated sodium chloride solution (600 ml). After drying the ether phase overnight over anhydrous sodium sulfate, filtration and concentration of the filtrate affords an orange gum. Separation of the isomeric mixture by preparative high pressure liquid chromatography using 40% ethyl acetate/hexane as solvent affords the cis-isomer as a clear yellow gum in which crystals eventually formed upon standing. The gum is triturated with a mixture of petroleum ether containing a little ether. The colorless solid is filtered, washed and dried to afford the cis-isomer mp 54.5°-57.5° C.

Workup

  1. customthe temperature below 10° C.
  2. additionduring the addition
  3. stirringAfter stirring overnight at room temperature
  4. additionis cautiously added
  5. extractionThe mixture is extracted with ether (3×600 ml)
  6. customThe solvent is removed in vacuo from the organic extracts
  7. customthe residue is partitioned between ether (1200 ml) and saturated sodium chloride solution (600 ml)
  8. dry with materialAfter drying the ether phase overnight
  9. filtrationover anhydrous sodium sulfate, filtration and concentration of the filtrate
  10. customaffords an orange gum
  11. customSeparation of the isomeric mixture by preparative high pressure liquid chromatography
  12. customaffords the cis-isomer as a clear yellow gum in which crystals
  13. customeventually formed
  14. customThe gum is triturated with a mixture of petroleum ether containing a little ether
  15. filtrationThe colorless solid is filtered
  16. washwashed
  17. customdried
  18. customto afford the cis-isomer mp 54.5°-57.5° C.

Sources & evidence

ORD record
ord-a311f4c4eaaa4b11abb6c2f4cf0a138b
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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