Water → {1-[1-(benzyloxy)-1H-pyrazol-5-yl]-2-ethylbutyl}amine

HRID 2243152Notes

Reaction equation

HRID 2243152 reaction equation
[N:1]([CH:4]([C:10]1[N:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:13]=[CH:12][CH:11]=1)[CH:5]([CH2:8][CH3:9])[CH2:6][CH3:7])=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:16]([O:15][N:14]1[C:10]([CH:4]([NH2:1])[CH:5]([CH2:8][CH3:9])[CH2:6][CH3:7])=[CH:11][CH:12]=[N:13]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 866000085-(1-Azido-2-ethylbutyl)-1-(benzyloxy)-1H-pyrazole

Product 1

HCID 68595201{1-[1-(benzyloxy)-1H-pyrazol-5-yl]-2-ethylbutyl}amineYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(1-Azido-2-ethylbutyl)-1-(benzyloxy)-1H-pyrazole (0.269 g, 0.90 mmol) was dissolved in THF (20 mL). Distilled water (0.40 mL, 22.5 mmol) was added, followed by triphenyl phosphine (0.590 g, 2.25 mmol). The mixture was refluxed for 2 h, cooled to ambient temperature and concentrated in vacuo. This produced a crude oil that was purified on a Biotage column (hexane/EtOAc, 1:1) to afford the product as a colorless oil (0.188 g, 76%). Mass Spectrum (+ESI): 274.2 (M+H)+.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. concentrationconcentrated in vacuo
  3. customThis produced a crude oil that
  4. customwas purified on a Biotage column (hexane/EtOAc, 1:1)

Sources & evidence

ORD record
ord-625fd1fa685b4e19843a82b00606ea45
Source dataset
uspto-grants-2010_03
Patent number
US07674813B2

Reaction notes

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