10-Formyl-8-aza-bicyclo[4.3.1]decane-8-carboxylic acid tert-butyl ester → 8-Tert-butoxycarbonyl-8-azabicyclo[4.3.1]decane-10-carboxylic acid

HRID 1455548Notes

Reaction equation

HRID 1455548 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:16][CH:15]2[CH:17]([CH:18]=[O:19])[CH:10]([CH2:11][CH2:12][CH2:13][CH2:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O.O.O.O.O.C(OO)(=O)C1C(=CC=CC=1)C(O)=[O:30].[Mg]>CCO.O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]2[CH:17]([C:18]([OH:30])=[O:19])[CH:15]([CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:16]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5742970010-Formyl-8-aza-bicyclo[4.3.1]decane-8-carboxylic acid tert-butyl esterHCID 86597096Magnesium monoperoxyphthalic acid hexahydrate

Product 1

HCID 684430478-Tert-butoxycarbonyl-8-azabicyclo[4.3.1]decane-10-carboxylic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

2.86 g of 10-formyl-8-aza-bicyclo[4.3.1]decane-8-carboxylic acid tert-butyl ester and 5.8 g of magnesium monoperoxyphthalic acid hexahydrate in 170 ml of EtOH/H2O (1:1) are stirred at RT. The mixture obtained is diluted with EtAc. The mixture obtained is extracted with aqueous 1M HCl and brine. The organic layer obtained is dried, solvent is evaporated and the evaporation residue is crystallized from MeOH/H2O. 8-aza-bicyclo[4.3.1]decane-8,10-dicarboxylic acid 8-tert-butyl ester is obtained. m.p.: 218-222°; 13C-NMR: 179.88, 155.31, 80.00, 52.43, 50.98, 47.63, 33.14, 32.31, 28.91, 27.06.

Workup

  1. customThe mixture obtained
  2. additionis diluted with EtAc
  3. customThe mixture obtained
  4. extractionis extracted with aqueous 1M HCl and brine
  5. customThe organic layer obtained
  6. customis dried
  7. customsolvent is evaporated
  8. customthe evaporation residue is crystallized from MeOH/H2O

Sources & evidence

ORD record
ord-43d2d1910c07479fa724d4f84cbbfbb0
Source dataset
uspto-grants-2009_01
Patent number
US07482462B2

Reaction notes

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