Iodoethane → (4R)-1-Boc-4-ethoxy-L-proline

HRID 1581712Notes

Reaction equation

HRID 1581712 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:14][C@H:13]([OH:15])[CH2:12][C@H:11]1[C:16]([OH:18])=[O:17])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:19](I)[CH3:20]>C1COCC1>[C:3]([O:7][C:8]([N:10]1[CH2:14][C@H:13]([O:15][CH2:19][CH3:20])[CH2:12][C@H:11]1[C:16]([OH:18])=[O:17])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 15222301(4R)-1-Boc-4-ethoxy-L-prolineYield 82.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.72 g of 60% sodium hydride in oil are added, under a nitrogen atmosphere, to a solution of 5 g of (2S,4R)-1-(tert-butoxycarbonyl)-4-hydroxy-2-pyrrolidinecarboxylic acid in 100 ml of THF, and the mixture is stirred for 45 minutes at RT. 3.27 g of ethyl iodide are then added, the mixture is refluxed for 3 hours and stirred for 18 hours while allowing the temperature to return to RT. The reaction mixture is concentrated under vacuum, the residue is taken up in 5% KHSO4 solution and extracted with EtOAc, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum. 4.5 g of the expected product are obtained in the form of an oil.

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. stirringstirred for 18 hours
  3. customto return to RT
  4. concentrationThe reaction mixture is concentrated under vacuum
  5. extractionextracted with EtOAc
  6. dry with materialthe organic phase is dried over Na2SO4
  7. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-1d96e562cf584bf3bad2e59976a4e0f2
Source dataset
uspto-grants-2004_05
Patent number
US06730695B2

Reaction notes

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