Ethanol → 1-Azabicyclo(2.2.2)octane-3-carbonitrile

HRID 1073113Notes

Reaction equation

HRID 1073113 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=O)[CH2:2]2.S([CH2:20][N+:21]#[C-])(C1C=CC(C)=CC=1)(=O)=O.C(O)C.CC(C)([O-])C.[K+]>C(COC)OC>[C:20]([CH:3]1[CH:4]2[CH2:7][CH2:8][N:1]([CH2:6][CH2:5]2)[CH2:2]1)#[N:21]

Participants

6

Reactant 4

HCID 702EthanolHCID 195073-QuinuclidinoneHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxide

Product 1

HCID 1428651-Azabicyclo(2.2.2)octane-3-carbonitrileYield 74%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
4 °C

Procedure

A mixture of 3-quinuclidinone (12.5 g; 0.10 moles), tosylmethyl isocyanide (25.4 g; 0.13 moles) and dry ethanol (10 ml; 0.17 moles) in dry dimethoxyethane (350 ml) was cooled in ice and treated portionwise with potassium t-butoxide (28.0 g; 0.25 moles) while maintaining the temperature between 5° C. and 10° C. After addition was complete the ice bath was removed and stirring was continued for a further 30 min. The reaction was then heated at 4° C. for 2.5 h. After cooling, the precipitate was filtered off and the filtrate concentrated in vacuo. Purification on neutral alumina (Brockmann grade 1) using 2% methanol in ethyl acetate as eluant afforded the title compound as a syrup (10.0 g: 74%) which crystallised on cooling.

Workup

  1. temperaturewas cooled in ice
  2. temperaturewhile maintaining the temperature between 5° C. and 10° C
  3. additionAfter addition
  4. customwas removed
  5. temperatureAfter cooling
  6. filtrationthe precipitate was filtered off
  7. concentrationthe filtrate concentrated in vacuo
  8. customPurification on neutral alumina (Brockmann grade 1)

Sources & evidence

ORD record
ord-961b427036834866a204bcc7a2be52ce
Source dataset
uspto-grants-1990_11
Patent number
US04968691

Reaction notes

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