1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-Cyclopropyl-prop-2-ynylazide

HRID 1827487Notes

Reaction equation

HRID 1827487 reaction equation
[CH:1]1([C:4]#[C:5][CH2:6]O)[CH2:3][CH2:2]1.C1C=CC(P([N:22]=[N+:23]=[N-:24])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.CCCCCC.C(Cl)Cl>[CH:1]1([C:4]#[C:5][CH2:6][N:22]=[N+:23]=[N-:24])[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 27937573-Cyclopropylprop-2-yn-1-ol

Product 1

HCID 221365273-Cyclopropyl-prop-2-ynylazide

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

3-Cyclopropyl-prop-2-yn-1-ol (3.28 g, 34.1 mmol) was dissolved in 40 mL toluene, DPPA (11.26 g, 40.9 mmol) was added, followed with DBU (6.24 g, 40.9 mmol) while maintaining temperature with a water bath. The mixture was stirred at room temperature for one hour and was diluted with 100 mL hexane and 15 mL CH2Cl2. The mixture was washed with water four times and once with brine, dried over Na2SO4, filtered and concentrated under rotovap with cold water bath to remove most of organic solvent leaving some toluene (product volatile). The residual oil was used for the next step.

Workup

  1. temperaturewhile maintaining temperature with a water bath
  2. washThe mixture was washed with water four times and once with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under rotovap with cold water bath
  6. customto remove most of organic solvent
  7. customleaving some toluene (product volatile)

Sources & evidence

ORD record
ord-3bc2da9d109c4ff681fab09937e5e9ec
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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