Triphenylphosphine → HCID 13341551, compound

HRID 1981125Notes

Reaction equation

HRID 1981125 reaction equation
[N:1]([CH:4]1[CH2:16][N:7]2[CH2:8][CH2:9][CH2:10][CH:11]([C:12]([O:14]C)=[O:13])[N:6]2[C:5]1=[O:17])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[NH2:1][CH:4]1[CH2:16][N:7]2[CH2:8][CH2:9][CH2:10][CH:11]([C:12]([OH:14])=[O:13])[N:6]2[C:5]1=[O:17]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 13341556HCID 13341556, compound

Product 1

HCID 13341551HCID 13341551, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.95 g of methyl 2-azido-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate (racemate B) and 1.05 g of triphenylphosphine in 20 ml of dioxane were stirred at room temperature for 1 hour and the mixture was then evaporated. The residue was treated with 40 ml of 2N aqueous ammonia at 50° C. for 2.5 hours and the precipitated triphenyl phosphine oxide was removed by filtration. Evaporation then yielded 0.53 g (66%) of 2-amino-hexahydro-3-oxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylic acid (racemate B) in the form of a white solid which, after recrystallization from aqueous methanol, melted at 228°-230° C. (decomposition).

Workup

  1. customthe mixture was then evaporated
  2. additionThe residue was treated with 40 ml of 2N aqueous ammonia at 50° C. for 2.5 hours
  3. customthe precipitated triphenyl phosphine oxide was removed by filtration
  4. customEvaporation

Sources & evidence

ORD record
ord-f429d397921e42308f9784ee113b69a6
Source dataset
uspto-grants-1985_04
Patent number
US04512924

Reaction notes

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