Water → HCID 59570926, compound

HRID 2192926Notes

Reaction equation

HRID 2192926 reaction equation
[C:1]1([C@H:7]2[C@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10][C:9]3([CH2:22][CH2:21][CH:20]([CH2:23]S(OC)(=O)=O)[CH2:19][CH2:18]3)[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-:29].[Na+].O.C(OCC)(=O)C>CC(C)=O>[I:29][CH2:23][CH:20]1[CH2:21][CH2:22][C:9]2([O:8][C@@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:10]2)[CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 8857Ethyl AcetateHCID 86647485HCID 86647485, compound

Product 1

HCID 59570926HCID 59570926, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl [(2S,3S)-2,3-diphenyl-1,4-dioxaspiro[4.5]dec-8-yl]methanesulfonate (58.6 g) in acetone (800 mL) was added sodium iodide (52.3 g) at room temperature. The mixture was heated under reflux overnight and again cooled to room temperature. To the reaction mixture were added water and ethyl acetate. The organic layer was separated, sequentially washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dried over anhydrous magnesium sulfate. The crude product obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=1:0-50:1-30:1-10:1) to obtain (2S,3S)-8-(iodomethyl)-2,3-diphenyl-1,4-dioxaspiro[4.5]decane (40.6 g) as a pale yellow oily substance.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. customThe organic layer was separated
  4. washsequentially washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe crude product obtained by concentration under reduced pressure
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=1:0-50:1-30:1-10:1)

Sources & evidence

ORD record
ord-5ebc639fd6cd46899df73260cadfb302
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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