Diiodomethane → HCID 18670642, compound

HRID 1059354Notes

Reaction equation

HRID 1059354 reaction equation
[CH2:1]([Zn]CC)C.ICI.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH:20]=[C:19]([CH2:22][OH:23])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].[Cl-].[NH4+]>ClCCl>[C:9]([O:13][C:14]([N:16]1[CH2:17][CH2:18][C:19]2([CH2:22][OH:23])[CH:20]([CH2:1]2)[CH2:21]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 225944841,1-Dimethylethyl 3,6-dihydro-4-(hydroxymethyl)-1(2H)-pyridinecarboxylateHCID 178418750HCID 178418750, compound

Product 1

HCID 18670642HCID 18670642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under ice-cooling, 15.3 ml of diethylzinc and 6.7 g of diiodomethane were added to 130 ml of dichloromethane. After further adding a solution of 1.07 g of 1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridine-4-methanol in dichloromethane (20 ml), the resulting mixture was stirred at room temperature overnight. Then the reaction mixture was poured into saturated ammonium chloride, extracted with ethyl acetate, 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 90 mg of the title compound as a colorless oily substance.

Workup

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

Sources & evidence

ORD record
ord-97bef62a970e4de5b8cb1a84b2432afc
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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