Iodoethane → HCID 90308911, compound

HRID 2283686Notes

Reaction equation

HRID 2283686 reaction equation
I[CH2:2][CH3:3].[OH:4][CH2:5][C@H:6]1[C@H:10]([CH3:11])[O:9][C:8]([CH3:13])([CH3:12])[N:7]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[H-].[Na+]>CN(C=O)C>[CH2:2]([O:4][CH2:5][C@H:6]1[C@H:10]([CH3:11])[O:9][C:8]([CH3:12])([CH3:13])[N:7]1[C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 398718101,1-Dimethylethyl (4S,5S)-4-(hydroxymethyl)-2,2,5-trimethyl-3-oxazolidinecarboxylate

Product 1

HCID 90308911HCID 90308911, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodoethane (0.80 mL) was added to a solution of (4S,5S)-tert-butyl 4-(hydroxymethyl)-2,2,5-trimethyloxazolidine-3-carboxylate (1.23 g), which can be synthesized by a method described in Bioorganic Chemistry 36 (2008) 4-15, in DMF (10 mL). Sodium hydride (60% in oil, 300 mg) was added under ice-cooling. Thereafter, the ice bath was removed, and the reaction solution was stirred at room temperature for 1 hour. Water and ethyl acetate were added to the reaction solution. After separation, the organic layer was washed with water twice. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain (4S,5S)-tert-butyl 4-(ethoxymethyl)-2,2,5-trimethyloxazolidine-3-carboxylate as light yellow amorphous.

Workup

  1. customcan be synthesized by a method
  2. temperaturecooling
  3. customThereafter, the ice bath was removed
  4. additionWater and ethyl acetate were added to the reaction solution
  5. customAfter separation
  6. washthe organic layer was washed with water twice
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. customthe solvent was evaporated under vacuum
  9. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-bbef86a61d024a999d0cb11af842c646
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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