Iodoethane → HCID 18657889, compound

HRID 1492825Notes

Reaction equation

HRID 1492825 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH:21]1[CH2:25][NH:24][C:23](=[O:26])[CH2:22]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:29](I)[CH3:30]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][Si:14]([C:17]([CH3:18])([CH3:19])[CH3:20])([CH3:16])[CH3:15])[CH2:10][C@H:9]1[CH:21]1[CH2:25][N:24]([CH2:29][CH3:30])[C:23](=[O:26])[CH2:22]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 57293964HCID 57293964, compound

Product 1

HCID 18657889HCID 18657889, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(2-pyrrolidon-4-yl)pyrrolidine (38.5 g, 0.1 mol, the compound of Reference Example 1-6) in tetrahydrofuran (200 ml) was added 60% sodium hydride in oil (4.2 g, 0.1 mol) under ice-cooling, and the mixture was stirred for 1 hour. To the mixture was added ethyl iodide (8 rag, 0.1 mol), and after stirring at room temperature overnight, the reaction mixture was concentrated. The residue was extracted with ethyl acetate (500 ml), and the mixture was washed with water (200 ml) followed by a saturated sodium chloride aqueous solution. After the extract was dried over anhydrous magnesium sulfate, the solvent was removed in vacuo, and the residue was purified by silica gel column chromatography (Wakogel™ C-300, chloroform) to obtain (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-(N-ethyl-2-pyrrolidon-4-yl)pyrrolidine (40.3 g, yield: 97.7%).

Workup

  1. temperaturecooling
  2. stirringafter stirring at room temperature overnight
  3. concentrationthe reaction mixture was concentrated
  4. extractionThe residue was extracted with ethyl acetate (500 ml)
  5. washthe mixture was washed with water (200 ml)
  6. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customthe residue was purified by silica gel column chromatography (Wakogel™ C-300, chloroform)

Sources & evidence

ORD record
ord-d428ad00eed54593bc28b49d60ccbc26
Source dataset
uspto-grants-1994_12
Patent number
US05374720

Reaction notes

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