Hydrochloric Acid → HCID 18670128, compound

HRID 1059356Notes

Reaction equation

HRID 1059356 reaction equation
[CH2:1]([Zn]CC)C.ICI.[CH2:9]([O:16][C:17]([N:19]1[CH2:24][CH:23]=[C:22]([CH2:25][CH2:26][OH:27])[CH2:21][CH2:20]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Cl-].[NH4+].Cl>ClC(Cl)C>[CH2:9]([O:16][C:17]([N:19]1[CH2:20][CH2:21][C:22]2([CH2:25][CH2:26][OH:27])[CH:23]([CH2:1]2)[CH2:24]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 18670409HCID 18670409, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 18670128HCID 18670128, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

Under ice-cooling, 75 ml of diethylzinc and 33.5 g of diiodomethane were added to 500 ml of dichloroethane. After further adding a solution of 6.53 g of 2-[1-(benzyloxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]ethanol in dichloroethane (20 ml), the resulting mixture was stirred at room temperature for 6 days. Then the reaction mixture was poured into a mixture of saturated ammonium chloride with 1 N hydrochloric acid, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate followed by filtration. After distilling off the solvent under reduced pressure, the obtained residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 1.22 g of the title compound as an oily substance.

Workup

  1. temperatureUnder ice-cooling
  2. washwashed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfollowed by filtration
  5. distillationAfter distilling off the solvent under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5ec271335f2e47a8b2f6cffcb18ed6cc
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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