1,2-Dimethoxyethane → 1-Azabicyclo(2.2.2)octane-3-carbonitrile

HRID 2107945Notes

Reaction equation

HRID 2107945 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(COC)OC.CC(C)([O-])C.[K+]>C(O)C>[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 80711,2-DimethoxyethaneHCID 195073-QuinuclidinoneHCID 161915Tosylmethyl isocyanideHCID 23665647Potassium tert-butoxide

Product 1

HCID 1428651-Azabicyclo(2.2.2)octane-3-carbonitrileYield 159,618.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Quinuclidinone (28.8 g, 0.23 mmol) and tosylmethyl isocyanide (58.4 g, 0.30 mol) were dissolved in 23 ml of absolute ethanol and 800 ml of dimethoxyethane and cooled to 0° C. Potassium t-butoxide (64.4 g, 0.57 mol) was added portionwise, and the reaction continued stirring at 0° C. for 30 minutes, then heated at 40° C. for 30 minutes. The reaction was cooled to room temperature and stirred for 16 hours. The reaction was filtered and the filtrate was concentrated in vacuo to afford a clear, golden brown oil (50 g) which was chromatographed on alumina eluting with ethyl acetate thus affording the title product, 23.3 g (74%).

Workup

  1. temperatureheated at 40° C. for 30 minutes
  2. temperatureThe reaction was cooled to room temperature
  3. stirringstirred for 16 hours
  4. filtrationThe reaction was filtered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f202c459df434fc080f07787770c5034
Source dataset
uspto-grants-1990_06
Patent number
US04937239

Reaction notes

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