1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-[(1R)-1-azidoethyl]-1-benzothiophene

HRID 1691669Notes

Reaction equation

HRID 1691669 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C@@H:10](O)[CH3:11])=[CH:2]1.C1C=CC(P([N:27]=[N+:28]=[N-:29])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C@H:10]([N:27]=[N+:28]=[N-:29])[CH3:11])=[CH:2]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 25128401(1S)-1-(1-benzothiophen-3-yl)ethan-1-ol

Product 1

HCID 866386933-[(1R)-1-azidoethyl]-1-benzothiopheneYield 93.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The process was carried out with reference to a method of Thompson, et al. (J. Org. Chem. 1993, 58, 5886). Under an argon atmosphere, a mixture of 5.50 g of (1S)-1-(1-benzothiene-3-yl)ethanol and 7.98 g of DPPA was dissolved in toluene, and 5.54 mL of DBU was then added thereto in an ice bath. After stirring for 30 min under ice-cooling, it was further stirred at room temperature for 15 hours. The reaction mixture was washed with water and 1 M hydrochloric acid in this order, and then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 5.86 g of (1R)-1-(1-benzothiene-3-yl)ethylazide as a colorless oily substance. EI: 203

Workup

  1. temperaturecooling
  2. stirringit was further stirred at room temperature for 15 hours
  3. washThe reaction mixture was washed with water and 1 M hydrochloric acid in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-2ef536de7a7641468a1b9a590bb03c15
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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