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1,4-Dioxane hydrochloride → Octahydroindolizin-7-one

HRID 9887
Notes
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Reaction equation

HRID 9887 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][C:14](=[O:27])[CH2:15][CH2:16]S(C1C=CC(C)=CC=1)(=O)=O)=O)(C)(C)C.Cl.O1CCOCC1>CO>[CH2:10]1[CH:9]2[N:8]([CH2:16][CH2:15][C:14](=[O:27])[CH2:13]2)[CH2:12][CH2:11]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 21988484(+/-)-1-(t-Butoxycarbonyl)-2-[4-(p-toluenesulfonyl)-2-oxobutyl]pyrrolidine

Product 1

HCID 11240524Octahydroindolizin-7-oneYield 65.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

(±)-1-(t-Butoxycarbonyl)-2-[4-(p-toluenesulfonyl)-2-oxobutyl]pyrrolidine (322 mg (0.814 mmol), prepared as described in 1)) was dissolved in methanol (3.2 ml). To the solution was added a solution of 4N hydrochloric acid/dioxane (0.61 ml, 2.44 mmol), and the resulting mixture was stirred at 50° C. for 30 minutes. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure to remove solvents and any excess of hydrochloric acid. To the residue was added a saturated aqueous solution of sodium hydrogencarbonate and this 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. The residue was purified by column chromatography through alumina (eluent, ethyl acetate), to give the title compound (74 mg) as a light brown oil (yield 65%).

Workup

  1. concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure
  2. customto remove solvents
  3. additionTo the residue was added a saturated aqueous solution of sodium hydrogencarbonate
  4. extractionthis was extracted with dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by column chromatography through alumina (eluent, ethyl acetate)

Sources & evidence

ORD record
ord-834874432cb64e90b07ca52638ef6387
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091352B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes