Allyl Alcohol → HCID 178458596, compound

HRID 1951291Notes

Reaction equation

HRID 1951291 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([OH:23])[CH:21]=[CH2:22].O[C:25]1[NH:29][N:28]=[C:27]([N:30]2[C:38](=[O:39])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]2=[O:40])[CH:26]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CN(C=O)C>[CH2:20]([O:23][C:25]1[NH:29][N:28]=[C:27]([N:30]2[C:31](=[O:40])[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:38]2=[O:39])[CH:26]=1)[CH:21]=[CH2:22]

Participants

6

Reactant 4

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178514959HCID 178514959, compound

Product 1

HCID 178458596HCID 178458596, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of triphenylphosphine (2.75 g, 10.5 mmol), allyl alcohol (0.714 ml, 10.5 mmol), and 2-(5-hydroxy-1H-pyrazol-3-yl)isoindoline-1,3-dione (2.000 g, 8.73 mmol) in DMF (25 mL) at RT was slowly added DIAD (2.04 ml, 10.5 mmol). After 18 hrs the solution was concentrated in vacuo, diluted with EtOAc, and washed with water and brine. The organic fraction was dried with sodium sulfate, concentrated in vacuo, and purified by silica gel chromatography using 40-70% Hexanes:EtOAc to afford 2-(5-(allyloxy)-1H-pyrazol-3-yl)isoindoline-1,3-dione as a light yellow solid. MH+=270.1. Step 2B: To a mixture of 2-(5-(allyloxy)-1H-pyrazol-3-yl)isoindoline-1,3-dione (0.684 g, 2.54 mmol) in EtOH (10 mL) at RT was added anhydrous hydrazine (0.319 ml, 10.2 mmol). The solution was heated at 50° C. for 18 hrs before cooling to 0° C. The resulting precipitate was removed by filtration. The filtrate was concentrated in vacuo to afford crude 5-(allyloxy)-1H-pyrazol-3-amine that was advanced without further purification. MS: Found M+H+=147.2.

Workup

  1. concentrationAfter 18 hrs the solution was concentrated in vacuo
  2. additiondiluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialThe organic fraction was dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-5c80fca85a8f4461972ce037a6ee0f45
Source dataset
uspto-grants-2013_03
Patent number
US08404694B2

Reaction notes

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