Sodium Iodide → Iodomethyl 2-(1-(tert-butoxycarbonyl)-4-piperidyl)-ethyl carbonate

HRID 852339Notes

Reaction equation

HRID 852339 reaction equation
[C:1](=[O:21])([O:5][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[O:2][CH2:3]Cl.[I-:22].[Na+]>CC(C)=O>[C:1](=[O:21])([O:5][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)[O:2][CH2:3][I:22]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 69348251Chloromethyl 2-(1-(tert-butoxycarbonyl)-4-piperidyl)-ethyl carbonate

Product 1

HCID 69576965Iodomethyl 2-(1-(tert-butoxycarbonyl)-4-piperidyl)-ethyl carbonate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

Chloromethyl 2-(1-(tert-butoxycarbonyl)-4-piperidyl)-ethyl carbonate (4.9 g) was added to a solution of sodium iodide (9 g) in acetone (20 ml). After stirring at 40° C. for 2.5 hours the reaction mixture was cooled to room temperature, filtered and evaporated in vacuo. The residue was taken up in dichloromethane, washed with aqueous sodium bicarbonate and sodium thiosulfate, dried over magnesium sulfate, filtered and evaporated in vacuo. Purification on silica gel with hexane/ethyl acetate (2:1) as eluent gave the title compound as a light yellow oil.

Workup

  1. temperaturewas cooled to room temperature
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. washwashed with aqueous sodium bicarbonate and sodium thiosulfate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customPurification on silica gel with hexane/ethyl acetate (2:1) as eluent

Sources & evidence

ORD record
ord-44233d549d1e400681905d6d8b37cd8b
Source dataset
uspto-grants-2007_08
Patent number
US07253193B2

Reaction notes

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