1,2-Dibromoethane → HCID 22881085, compound

HRID 725951Notes

Reaction equation

HRID 725951 reaction equation
[Mg].BrCCBr.Br[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1.[C:17]([O:21][C:22]([N:24]1[CH2:30][C@H:29]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:28][C@H:25]1[CH:26]=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(OCC)C.O1CCCC1.O>[C:17]([O:21][C:22]([N:24]1[CH2:30][C@H:29]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH2:28][C@H:25]1[CH:26]([OH:27])[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 78391,2-DibromoethaneHCID 113722-BromonaphthaleneHCID 5462224MagnesiumHCID 10969557tert-Butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-formylpyrrolidine-1-carboxylate

Product 1

HCID 22881085HCID 22881085, compoundYield 67.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Magnesium (3.4 g) and a solution of 1,2-dibromoethane (5.3 ml, 60.8 mmol) in diethyl ether (40 ml) were successively added to a solution of 2-bromonaphthalene (12.6 g, 60.8 mmol) in diethyl ether (160 ml) at room temperature in a nitrogen stream and this reaction solution was refluxed under heating for 2.5 hours. The reaction solution was gradually cooled and a solution of (2S,4R)-N-t-butoxycarbonyl-4-(t-butyldimethylsiloxy)prolinal (10 g, 30.4 mmol) in tetrahydrofuran (50 ml) was added dropwise thereto under cooling with ice. Then, the reaction solution was stirred at room temperature for 1 hour. After addition of water, the reaction solution was concentrated in vacuo and was poured into a liquid mixture of ethyl acetate with water. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting oily residue was subjected to silica gel column chromatography (Wakogel™ C-300, heptane-ethyl acetate=4:1) to give (2S,4R)-N-t-butoxycarbonyl-4-t-butyldimethylsiloxy-2-[hydroxy(2-naphthyl)methyl]pyrrolidine (9.38 g, yield: 67.5%) as a yellow oily substance.

Workup

  1. temperaturethis reaction solution was refluxed
  2. temperatureunder heating for 2.5 hours
  3. temperatureThe reaction solution was gradually cooled
  4. temperatureunder cooling with ice
  5. concentrationthe reaction solution was concentrated in vacuo
  6. additionwas poured into a liquid mixture of ethyl acetate with water
  7. washThe organic layer was washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8abaa7c821214915aced54f97adcfcb5
Source dataset
uspto-grants-1998_01
Patent number
US05707987

Reaction notes

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