Diethyl Ether → HCID 68693044, compound

HRID 2236527Notes

Reaction equation

HRID 2236527 reaction equation
C([CH:5]1[C@H:9]([O:10][CH3:11])[CH2:8][CH2:7][N:6]1[C:12]([O-])=O)(C)(C)C.CCOCC.[N+:20]([C:23]1[CH:30]=[CH:29][C:26](CBr)=[CH:25][CH:24]=1)([O-:22])=[O:21]>Cl>[CH3:11][O:10][CH:9]1[CH2:8][CH2:7][N:6]([CH2:12][C:26]2[CH:29]=[CH:30][C:23]([N+:20]([O-:22])=[O:21])=[CH:24][CH:25]=2)[CH2:5]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 660114-Nitrobenzyl bromideHCID 86619577HCID 86619577, compound

Product 1

HCID 68693044HCID 68693044, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

An amount of 1.8 g (9.02 mmol) of tert-butyl-(3R)-3-methoxypyrrolidin-1-yl carboxylate is stirred in concentrated hydrogen chloride (10 mL) for two hours. Anhydrous ether (100 mL) is added and stirred for additional 30 minutes. The ether is decanted and this is repeated three times. The mixture is neutralized with excess triethylamine and after evaporating to dryness, the mixture is re-dissolved in methylene chloride (100 mL) and 1.5 g (6.94 mmol) of 4-nitrobenzylbromide is added and refluxed for two hours. After cooling, the mixture is washed three times with aqueous sodium bicarbonate, dried over magnesium sulfate and evaporated to give 1.1 g (67% yield) of the nitro intermediates as a yellow oil.

Workup

  1. customThe ether is decanted
  2. customafter evaporating to dryness
  3. dissolutionthe mixture is re-dissolved in methylene chloride (100 mL)
  4. temperaturerefluxed for two hours
  5. temperatureAfter cooling
  6. washthe mixture is washed three times with aqueous sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-c6e0e8c0bb4247b1afcecad415209c4b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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