Hydrochloric Acid → Octahydroindolizin-7-one

HRID 9885

Reaction equation

HRID 9885 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][C:14](=[O:17])[CH:15]=[CH2:16])=O)(C)(C)C.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:10]1[CH:9]2[N:8]([CH2:16][CH2:15][C:14](=[O:17])[CH2:13]2)[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21988503Tert-butyl 2-(2-oxobut-3-EN-1-YL)pyrrolidine-1-carboxylate

Product 1

HCID 11240524Octahydroindolizin-7-oneYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

(±)-1-(t-Butoxycarbonyl)-2-(2-oxo-3-butenyl)pyrrolidine (140 mg (0.59 mmol), prepared as described in 2)) was dissolved in tetrahydrofuran (2 ml). To the solution was added an aqueous solution of 1N hydrochloric acid (1.76 ml, 1.76 mmol), and the resulting mixture was stirred at 70° C. for 4 hours. At the end of this time, to the reaction mixture was added a saturated aqueous solution of sodium hydrogencarbonate and the resulting mixture was extracted with dichloromethane. 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 (76 mg) as a light brown oil (yield 93%).

Workup

  1. extractionthe resulting mixture was extracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-bd1629c0454e45928b744802850b9f19
Source dataset
uspto-grants-2006_08
Patent number
US07091352B2

Linked notes

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