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Potassium Carbonate → Diethyl 2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)malonate

HRID 8581
Notes
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Reaction equation

HRID 8581 reaction equation
Br[CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH:19]12[O:26][CH:23]([CH2:24][CH2:25]1)[CH2:22][NH:21][CH2:20]2>C(#N)C>[CH:23]12[O:26][CH:19]([CH2:25][CH2:24]1)[CH2:20][N:21]([CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:22]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonateHCID 120692318-Oxa-3-azabicyclo[3.2.1]octane

Product 1

HCID 21983519Diethyl 2-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)malonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

4.72 g (19.8 mmol) of diethyl 2-bromomalonate are introduced into 30 ml of acetonitrile. Then 3.82 g (27.7 mmol) of potassium carbonate and 2.46 g (21.7 mmol) of 8-oxa-3-azabicyclo[3.2.1]octane from step 4 are added. The suspension is stirred at 50° C. overnight. This is followed by filtration with suction and evaporation of the filtrate to dryness in a rotary evaporator. The residue is employed without further purification in the next stage.

Workup

  1. filtrationThis is followed by filtration with suction and evaporation of the filtrate to dryness in a rotary evaporator
  2. customThe residue is employed without further purification in the next stage

Sources & evidence

ORD record
ord-e6c92f751d374d10a3c43575d67b3af8
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091198B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes