1,8-Diazabicyclo(5.4.0)undec-7-ene → (5S)-5-azido-2-iodo-5-(6-quinolyl)-2-pentene

HRID 348253Notes

Reaction equation

HRID 348253 reaction equation
[I:1][C:2](=[CH:4][CH2:5][C@H:6]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)O)[CH3:3].C1(P([N:32]=[N+:33]=[N-:34])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:32]([C@H:6]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)[CH2:5][CH:4]=[C:2]([I:1])[CH3:3])=[N+:33]=[N-:34]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 86586613(5R)-2-iodo-5-(6-quinolyl)-5-hydroxy-2-pentene

Product 1

HCID 86586615(5S)-5-azido-2-iodo-5-(6-quinolyl)-2-pentene

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (5R)-2-iodo-5-(6-quinolyl)-5-hydroxy-2-pentene (1.74 g) in 30 mL of toluene is cooled to 0° C. and treated with diphenylphosphoryl azide (1.65 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.91 g) for 2 hours. The mix is warmed to ambient temperature and diluted with ethyl acetate. The solution is washed sequentially with water, sat. NaHCO3, and brine, then dried over MgSO4, filtered, and evaporated. The product is purified by SiO2 chromatography.

Workup

  1. washThe solution is washed sequentially with water, sat. NaHCO3, and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe product is purified by SiO2 chromatography

Sources & evidence

ORD record
ord-92f6eca90ea14f8ea19f69162926641f
Source dataset
uspto-grants-2007_02
Patent number
US07176235B2

Reaction notes

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