1,8-Diazabicyclo(5.4.0)undec-7-ene → Tert butyl 4-iodo-1-methyl-7-oxo-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate

HRID 527024Notes

Reaction equation

HRID 527024 reaction equation
[I:1][CH:2]1[CH:8]2[CH2:9][C:5]([CH3:18])([C:6](=[O:17])[N:7]2[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4][CH2:3]1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[I:1][C:2]1[CH:8]2[CH2:9][C:5]([CH3:18])([C:6](=[O:17])[N:7]2[C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:4][CH:3]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68008486Tert-butyl 4-iodo-1-methyl-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate2×

Product 1

HCID 86667435Tert butyl 4-iodo-1-methyl-7-oxo-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl 4-iodo-1-methyl-7-oxo-6-azabicyclo[3.2.1]octane-6-carboxylate, 52d, (7.6 g, 20.8 mmol) in 100 mL of toluene was added 1,8-diazabicyclo[5.4.0]undec-7-ene (6.2 mL, 41.6 mmol). The reaction was warmed to reflux and stirred overnight. The reaction was concentrated in vacuo and the resulting residue was purified by silica gel chromatography (4:1 Hexanes:EtOAc), yielding 4.9 g of the desired product, 52e.

Workup

  1. temperatureThe reaction was warmed
  2. temperatureto reflux
  3. concentrationThe reaction was concentrated in vacuo
  4. customthe resulting residue was purified by silica gel chromatography (4:1 Hexanes:EtOAc)

Sources & evidence

ORD record
ord-8d9e7b23aa3348d49e5039a0e1265a29
Source dataset
uspto-grants-2016_05
Patent number
US09345708B2

Reaction notes

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