1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57448194, compound

HRID 1667600Notes

Reaction equation

HRID 1667600 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[CH2:14]O)([CH3:3])[CH3:2].C1C=CC(P([N:30]=[N+:31]=[N-:32])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[N:30]([CH2:14][C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=1[O:4][CH:1]([CH3:3])[CH3:2])=[N+:31]=[N-:32]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 28963963HCID 28963963, compound

Product 1

HCID 57448194HCID 57448194, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 8B (190 mg, 0.89 mmol) in THF (5 mL) at 0° C. was added DPPA (300 mg, 1.1 mmol) in THF (1 mL) and DBU (170 mg, 1.9 mmol). The cold bath was removed and the reaction was stirred at rt overnight. The reaction was then concentrated and purified via silica gel chromatography (0-15% ethyl acetate/hexane) to provide 8C (160 mg, 90%) and starting material (8B) (30 mg). 8C: LC-MS: 237.16 (M+H)+.

Workup

  1. customThe cold bath was removed
  2. concentrationThe reaction was then concentrated
  3. custompurified via silica gel chromatography (0-15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e939d4e025c0418ca19b6440a40d42f9
Source dataset
uspto-grants-2011_10
Patent number
US08044242B2

Reaction notes

Loading…