Sodium Iodide → 10-Formyl-8-aza-bicyclo[4.3.1]decane-8-carboxylic acid tert-butyl ester

HRID 1455547Notes

Reaction equation

HRID 1455547 reaction equation
C(O[C:6]([CH:8]([CH2:16][CH3:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]C)=O)(C)(C)C.[OH2:18].[OH2:19].[OH2:20].O.O.O.O.[Cl-].[Cl-].[Cl-].[Ce+3].[I-].[Na+].C[C:32]#[N:33]>>[C:8]([O:18][C:32]([N:33]1[CH2:6][CH:8]2[CH:16]([CH:17]=[O:20])[CH:13]([CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:14]1)=[O:19])([CH3:16])([CH3:9])[CH3:6]

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 21585214Cerium trichloride heptahydrateHCID 57517018Decane-8-carboxylic acid tert-butyl ester

Product 1

HCID 5742970010-Formyl-8-aza-bicyclo[4.3.1]decane-8-carboxylic acid tert-butyl ester

Procedure

4.8 g of 10-methoxymethylene-8-aza-blcyclo[4.3.1]decane-8-carboxylic acid tert-butyl ester are dissolved in 180 ml of CH3CN, 1.94 g of cerium trichloride heptahydrate and 390 mg of sodium iodide are added and the mixture obtained is stirred at 40° overnight. From the mixture obtained solvent is evaporated and the evaporation residue obtained is dissolved in EtAc. The mixture obtained is extracted with aqueous 1M HCl, aqueous, saturated NaHCO3-solution and brine. The organic layer obtained is dried, solvent is evaporated and the evaporation residue obtained is subjected to filtration over silica gel with EtAc/c-Hex (1:4→1:2). 10-Formyl-8-aza-bicyclo[4.3.1]decane-8-carboxylic acid tert-butyl ester is obtained. m.p.: 55-60°; 13C-NMR: 204.53, 155.28, 78.00, 55.40, 32.44, 32.12, 30.06, 28.89, 27.29.

Workup

  1. customthe mixture obtained
  2. customFrom the mixture obtained solvent
  3. customis evaporated
  4. customthe evaporation residue obtained
  5. dissolutionis dissolved in EtAc
  6. customThe mixture obtained
  7. extractionis extracted with aqueous 1M HCl
  8. customThe organic layer obtained
  9. customis dried
  10. customsolvent is evaporated
  11. customthe evaporation residue obtained
  12. filtrationis subjected to filtration over silica gel with EtAc/c-Hex (1:4→1:2)

Sources & evidence

ORD record
ord-8c21d475b5e142d1b579d341d04970d4
Source dataset
uspto-grants-2009_01
Patent number
US07482462B2

Reaction notes

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