Sodium Bicarbonate → HCID 58681494, compound

HRID 9888Notes

Reaction equation

HRID 9888 reaction equation
COC([CH:5]1[C:13](=[O:14])[CH2:12][C@H:11]2[N:7]([CH2:8][CH2:9][CH2:10]2)[C:6]1=[O:15])=O.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:10]1[C@@H:11]2[N:7]([C:6](=[O:15])[CH2:5][C:13](=[O:14])[CH2:12]2)[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 58681492HCID 58681492, compound

Product 1

HCID 58681494HCID 58681494, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

(8aS)-6-Methoxycarbonyl-1,2,3,5,6,7,8,8a-octahydroindolizin-5,7-dione (183 mg (0.87 mmol), prepared as described in 2)) was dissolved in an aqueous solution of 10% acetic acid (2 ml). The resulting mixture was stirred at 110° C. for 30 minutes, and then cooled to room temperature. To the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate and the mixture was made alkaline. The mixture was extracted with a solution of dichloromethane and isopropanol (4:1). The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure, to give the title compound (117 mg) as a pale brown oil (yield 87%).

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with a solution of dichloromethane and isopropanol (4:1)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-a08229d4402d4ef2a70f15be053e3cac
Source dataset
uspto-grants-2006_08
Patent number
US07091352B2

Reaction notes

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