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