Sodium Carbonate → 8-(2-Hydroxyethyl)-8-azabicyclo[3.2.1]octan-3-ol

HRID 1928994Notes

Reaction equation

HRID 1928994 reaction equation
Cl.[CH:2]12[NH:9][CH:6]([CH2:7][CH2:8]1)[CH2:5][CH:4]([OH:10])[CH2:3]2.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:18][CH2:19][OH:20]>C(O)C>[OH:20][CH2:19][CH2:18][N:9]1[CH:6]2[CH2:7][CH2:8][CH:2]1[CH2:3][CH:4]([OH:10])[CH2:5]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 108982-BromoethanolHCID 84401Endo-8-azabicyclo[3.2.1]octan-3-ol hydrochloride

Product 1

HCID 637695718-(2-Hydroxyethyl)-8-azabicyclo[3.2.1]octan-3-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

8-Aza-bicyclo[3.2.1]octan-3-ol hydrochloride (5.1 g, 31.45 mmol)) and sodium carbonate (13.3 g, 125.8 mmol) are suspended in 150 ml of ethanol at room temperature. 2-Bromo-ethanol (4.4 ml, 62.9 mmol) is added dropwise within 20 minutes and the reaction mixture is refluxed for 15 hours. After cooling to room temperature the reaction mixture is evaporated under reduced pressure. The mixture is stirred with 200 ml of DCM and filtered. The clear filtrate is dried over anhydrous sodium sulfate, filtered, evaporated under reduced pressure and dried at high vacuum.

Workup

  1. temperaturethe reaction mixture is refluxed for 15 hours
  2. customis evaporated under reduced pressure
  3. filtrationfiltered
  4. dry with materialThe clear filtrate is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customdried at high vacuum

Sources & evidence

ORD record
ord-739942d09da943e09f7c1370d8f3ef83
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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