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

HRID 1357415Notes

Reaction equation

HRID 1357415 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-2c7eace36d4942f69cdd5dc1f0c2de89
Source dataset
uspto-grants-2003_07
Patent number
US06589968B2

Reaction notes

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