Sodium hydride → (8-Methyl-8-azabicyclo[3.2.1]octan-3-ylidene)acetonitrile

HRID 356101Notes

Reaction equation

HRID 356101 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH3:14][N:15]1[CH:19]2[CH2:20][C:21]([CH2:23][CH:16]1[CH2:17][CH2:18]2)=O>O1CCOCC1>[C:1]([CH:3]=[C:21]1[CH2:23][CH:16]2[N:15]([CH3:14])[CH:19]([CH2:18][CH2:17]2)[CH2:20]1)#[N:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 79038Npc164516

Product 1

HCID 18940988(8-Methyl-8-azabicyclo[3.2.1]octan-3-ylidene)acetonitrileYield 102.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 1.95 g of diethyl cyanomethylphosphonate in 40 ml of dioxane was cooled to 10° C., followed by the addition of 0.44 g of sodium hydride (60%) in an argon gas atmosphere. A solution of 1.39 g of tropinone in 25 ml of dioxane was added dropwise to the resulting mixture at the same temperature, followed by stirring at room temperature for 1.5 hours. After the solvent was evaporated, water was added to the residue. The resulting mixture was extracted with chloroform, followed by drying over anhydrous potassium carbonate. The solvent was then evaporated, whereby 1.66 g of 3-cyanomethylene-8-methyl-8-azabicyclo[3.2.1]octane was obtained as the oily form.

Workup

  1. customAfter the solvent was evaporated
  2. additionwater was added to the residue
  3. extractionThe resulting mixture was extracted with chloroform
  4. dry with materialby drying over anhydrous potassium carbonate
  5. customThe solvent was then evaporated

Sources & evidence

ORD record
ord-e12905281a8543fa84e2b64e22388c8a
Source dataset
uspto-grants-1998_11
Patent number
US05834499

Reaction notes

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