Ethyl chloroformate → Ethyl 3-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylate

HRID 1277379Notes

Reaction equation

HRID 1277379 reaction equation
C[N:2]1[C@@H:7]2[CH2:8][C:9]([CH2:11][C@H:3]1[CH2:4][CH2:5][CH2:6]2)=[O:10].[CH2:12]([O:14][C:15](Cl)=[O:16])[CH3:13]>C1(C)C=CC=CC=1>[CH2:12]([O:14][C:15]([N:2]1[CH:7]2[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:11][C:9](=[O:10])[CH2:8]2)=[O:16])[CH3:13]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 6602484552-70-5

Product 1

HCID 54360990Ethyl 3-oxo-9-azabicyclo[3.3.1]nonane-9-carboxylateYield 86.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

186.8 g of pseudo-pelletierine and 264 g of freshly distilled chloroformic acid ethyl ester are slowly heated to a boil in 1 liter of absolute toluene within one hour. A vigorous evolution of gas sets in. The mixture is heated to a boil under reflux for a further 16 hours, then cooled and filtered. The filtrate is concentrated in a vacuum, and the residue is purified through vacuum distillation to obtain 223 g (86.5 percent) of light-yellow oil (b.p. 101° C. at 2.7 Pa.)

Workup

  1. temperatureThe mixture is heated to a boil
  2. temperatureunder reflux for a further 16 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in a vacuum
  6. distillationthe residue is purified through vacuum distillation

Sources & evidence

ORD record
ord-b93e97105d8a43c39cc48bd872095df6
Source dataset
uspto-grants-1981_07
Patent number
US04277472

Reaction notes

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