1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22464491, compound

HRID 1935448Notes

Reaction equation

HRID 1935448 reaction equation
[CH2:1]([S:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]O)[CH3:2].C1C=CC(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[N:26]([CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[S:3][CH2:1][CH3:2])=[N+:27]=[N-:28]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 12888291HCID 12888291, compound

Product 1

HCID 22464491HCID 22464491, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(ethylthio)benzyl alcohol (3.98 g, 23.6 mmol) in THF (48 mL) at 0° C. under Ar was added DPPA (6.1 mL, 28.4 mmol) followed by DBU (4.0 mL, 26.0 mmol). The reaction was allowed to warm to room temperature and stirred for 2 days. The solution was concentrated to an oil, which was taken up in EtOAc, and washed successively with 10% aqueous citric acid, saturated aqueous NaHCO3 solution and brine. The organic layer was dried over Na2SO4 and concentrated to an oil which was purified by silica gel chromatography (gradient elution with 100% hexanes to 5% EtOAc-hexanes). Concentration of the product fractions at reduced pressure afforded a pale yellow oil which was dried on a high vacuum line overnight to afford the title compound:

Workup

  1. concentrationThe solution was concentrated to an oil, which
  2. washwashed successively with 10% aqueous citric acid, saturated aqueous NaHCO3 solution and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated to an oil which
  5. customwas purified by silica gel chromatography (gradient elution with 100% hexanes to 5% EtOAc-hexanes)
  6. customConcentration of the product fractions at reduced pressure afforded a pale yellow oil which
  7. customwas dried on a high vacuum line overnight

Sources & evidence

ORD record
ord-2767305519604f999b284cc2c4ba5869
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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