Imidazole → HCID 15042006, compound

HRID 2371501Notes

Reaction equation

HRID 2371501 reaction equation
O[CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:43]I>C(OCC)(=O)C.C(Cl)Cl.CCCCCC.C(Cl)Cl.C1C=CC=CC=1>[I:43][CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:4]1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

Product 1

HCID 15042006HCID 15042006, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 21226138Dichloromethane ethylacetateSolventHCID 21226440Methylenechloride HexaneSolvent

Procedure

To a solution of 1.0 g (3.84 mmol) of tert-butyl [(4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-yl]acetate, 2.01 g (7.68 mmol) of triphenylphosphine, 0.523 g (7.68 mmol) of imidazole and 11.5 ml of anhydrous benzene was added 1.46 g (5.8 mmol) of iodine with stirring and cooling with ice, and then reacted for 2.5 hours at room temperature. The deposited crystal was filtered, and the obtained crystal was washed with ether. The filtrate and the washings were combined and distilled away under reduced pressure. The residue was purified by subjecting to silica gel column chromatography [eluent: hexane-methylene chloride (1:1), successively ethyl acetate-methylene chloride (1:9)]to give 1.41 g of tert-butyl [(4R,6S)-6-(iodomethyl)-2,2-dimethyl-1,3-dioxane-4-yl]acetate as syrups (yield: 99%).

Workup

  1. temperaturecooling with ice
  2. customreacted for 2.5 hours at room temperature
  3. filtrationThe deposited crystal was filtered
  4. washthe obtained crystal was washed with ether
  5. distillationdistilled away under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-e3b5014a03c54de6a61c5f2f571536c6
Source dataset
uspto-grants-1992_03
Patent number
US05093363

Reaction notes

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