Ethyl chloroformate → Ethyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate

HRID 1277381Notes

Reaction equation

HRID 1277381 reaction equation
C[N:2]1[CH:6]2[CH2:7][C:8]([CH2:10][CH:3]1[CH2:4][CH2:5]2)=[O:9].Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C1C=CC=CC=1>[CH2:15]([O:14][C:12]([N:2]1[CH:6]2[CH2:5][CH2:4][CH:3]1[CH2:10][C:8](=[O:9])[CH2:7]2)=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 79038Npc164516

Product 1

HCID 401882Ethyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateYield 88.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

56.5 g of tropinone are dissolved in 330 ml of anhydrous benzene and heatedto 70° C. under a nitrogen atmosphere. A solution of 88 g of freshly-distilled ethyl chloroformate in 200 ml of benzene is added dropwise within one hour, with stirring. After a further 4 hours' heating under reflux, cooling is effected, followed by filtration; the filtrate isconcentrated in a vacuum, and the residue is purified by vacuum distillation to obtain 70.75 g (88.4 percent) of (e) as colorless oil (b.p. 91° to 93° C. at 12 Pa.)

Workup

  1. customheatedto 70° C. under a nitrogen atmosphere
  2. temperatureAfter a further 4 hours' heating
  3. temperatureunder reflux
  4. temperaturecooling
  5. filtrationfollowed by filtration
  6. distillationthe residue is purified by vacuum distillation

Sources & evidence

ORD record
ord-f7f07dc6c86f46559f9bcc0e33b95e5e
Source dataset
uspto-grants-1981_07
Patent number
US04277472

Reaction notes

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