Ammonia → 2-((Tetrahydro-2H-pyran-2-YL)oxy)cyclopropane-1-carboxamide

HRID 496050Notes

Reaction equation

HRID 496050 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:10][CH:9]1[C:11]([O:13]CC)=O.[C-]#[N:17].[Na+].N>CO>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:10][CH:9]1[C:11]([NH2:17])=[O:13]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 8929Sodium CyanideHCID 22325102Ethyl 2-(oxan-2-yloxy)cyclopropane-1-carboxylate

Product 1

HCID 223251632-((Tetrahydro-2H-pyran-2-YL)oxy)cyclopropane-1-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In an autoclave, a solution of 0.25 mol of the compound obtained in Step 2, 2 g of sodium cyanide, 300 ml of a 2N solution of ammonia in methanol and 80 ml of liquid ammonia is heated at 65° C. for 5 days and is then concentrated to dryness. The residue is taken up in a mixture of dichloromethane/saturated potassium carbonate solution, filtered over Celite and then treated in conventional manner. After evaporating under reduced pressure, the residue is triturated in petroleum ether, filtered, rinsed and dried, allowing the expected product to be isolated.

Workup

  1. concentrationis then concentrated to dryness
  2. additionThe residue is taken up in a mixture of dichloromethane/saturated potassium carbonate solution
  3. filtrationfiltered over Celite
  4. additiontreated in conventional manner
  5. customAfter evaporating under reduced pressure
  6. customthe residue is triturated in petroleum ether
  7. filtrationfiltered
  8. washrinsed
  9. customdried
  10. customto be isolated

Sources & evidence

ORD record
ord-37dccb7e6302428a9e079c22d310f0b7
Source dataset
uspto-grants-2005_09
Patent number
US06943184B2

Reaction notes

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