Hydrochloric Acid → HCID 13039299, compound

HRID 851066Notes

Reaction equation

HRID 851066 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=[O:5])[CH3:2].[BH4-].[Na+].Cl.[H][H]>C(O)C.[Cl-].[Na+]>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][C@@H:9]([OH:12])[C@H:8]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20503534HCID 20503534, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13039299HCID 13039299, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 5234Sodium ChlorideSolvent

Procedure

To a solution of 48.4 g of 1-ethoxycarbonyl-3-phenyl-4-piperidone in 500 ml of denatured ethanol is added, dropwise at 0°-10° C. under nitrogen, a solution of 7.57 g of sodium borohydride in 325 ml of denatured ethanol, over a 30-minute period. After stirring overnight at room temperature the mixture is diluted with 1200 ml of saturated sodium chloride solution and stirred for one hour. The mixture is cautiously treated with 500 ml of 2 N hydrochloric acid and stirred until hydrogen evolution has slowed. The mixture is extracted with ether (3×600 ml) and the organic extracts concentrated in vacuo to a residue which was partitioned between ether (1200 ml) and saturated sodium chloride solution (600 ml). After drying the organic phase overnight over anhydrous sodium sulfate, removal of the solvent in vacuo affords a viscous orange gum. Purification of this crude mixture of isomers by high pressure liquid chromatography in 40% ethyl acetate/hexane affords the cis-isomer and trans-isomer as cloudy yellow gums. Trituration of the gummy trans-isomer with petroleum ether affords pure trans-isomer as a colorless solid, mp 49.5°-58° C.

Workup

  1. stirringstirred for one hour
  2. extractionThe mixture is extracted with ether (3×600 ml)
  3. concentrationthe organic extracts concentrated in vacuo to a residue which
  4. customwas partitioned between ether (1200 ml) and saturated sodium chloride solution (600 ml)
  5. customAfter drying the organic phase overnight
  6. customover anhydrous sodium sulfate, removal of the solvent in vacuo
  7. customaffords a viscous orange gum
  8. customPurification of this crude
  9. additionmixture of isomers by high pressure liquid chromatography in 40% ethyl acetate/hexane
  10. customaffords the cis-isomer and trans-isomer as cloudy yellow gums

Sources & evidence

ORD record
ord-f613fd27ef704c3185dc5edc458816ef
Source dataset
uspto-grants-1983_05
Patent number
US04382141

Reaction notes

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