Ethanolamine → 2-(2-Azaspiro[3.3]heptan-2-yl)ethanol

HRID 385868Notes

Reaction equation

HRID 385868 reaction equation
Br[CH2:2][C:3]1([CH2:7]Br)[CH2:6][CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[CH2:15]([CH2:17][NH2:18])[OH:16]>C(#N)C>[CH2:7]1[C:3]2([CH2:6][CH2:5][CH2:4]2)[CH2:2][N:18]1[CH2:17][CH2:15][OH:16]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 126511551,1-Bis(bromomethyl)cyclobutane

Product 1

HCID 450878752-(2-Azaspiro[3.3]heptan-2-yl)ethanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a three neck 3 L round bottom flask was added 1,1-bis(bromomethyl)cyclobutane (100 g, 0.43 mol), potassium carbonate (285 g, 2.06 mol), acetonitrile (1000 mL) and ethanolamine (37.8 g, 0.62 mol). The reaction mixture was heated to reflux for 2 days. The reaction mixture was concentrated to half volume and water was added (300 mL). The aqueous layer was extracted with dichloromethane (2×500 mL). The combined organic layers were washed with brine (200 mL), dried over sodium sulfate, filtered, and concentrated to afford the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 days
  3. concentrationThe reaction mixture was concentrated to half volume and water
  4. additionwas added (300 mL)
  5. extractionThe aqueous layer was extracted with dichloromethane (2×500 mL)
  6. washThe combined organic layers were washed with brine (200 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-111716eee8a7487994b87d197eedaf5d
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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