Cesium carbonate → Methyl 5-(tert-butoxycarbonylamino)-1-methylcyclohex-3-enecarboxylate

HRID 74997Notes

Reaction equation

HRID 74997 reaction equation
[CH3:1][C:2]12[CH2:17][CH:6]([N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:8]1=[O:9])[CH:5]=[CH:4][CH2:3]2.IC1C2CC(C)(C(=O)N2[C:27](OC(C)(C)C)=[O:28])CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO>[C:13]([O:12][C:10]([NH:7][CH:6]1[CH2:17][C:2]([CH3:1])([C:8]([O:28][CH3:27])=[O:9])[CH2:3][CH:4]=[CH:5]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68008024Tert-butyl 1-methyl-7-oxo-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylateHCID 86667435Tert butyl 4-iodo-1-methyl-7-oxo-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate

Product 1

HCID 67285544Methyl 5-(tert-butoxycarbonylamino)-1-methylcyclohex-3-enecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 1-methyl-7-oxo-6-azabicyclo[3.2.1]oct-3-ene-6-carboxylate, 52e, (4.93 g, 20.78 mmol) in MeOH (100 mL) was added cesium carbonate (13.54 g, 41.56 mmol). The reaction was stirred overnight and then concentrated in vacuo. The cesium salts were precipitated with Et2O and filtered. The ether filtrate was evaporated to give 5.5 g of a yellow oil that was used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe cesium salts were precipitated with Et2O
  3. filtrationfiltered
  4. customThe ether filtrate was evaporated

Sources & evidence

ORD record
ord-b4c8293e3e304bb4a76cf91d58d46185
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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