Ethanol → (S)-1,2,3,5,6,7,8,8a-octahydroindolizin-7-one

HRID 9890Notes

Reaction equation

HRID 9890 reaction equation
N1([C:6]2[CH2:14][C@H:13]3[N:9]([CH2:10][CH2:11][CH2:12]3)[C:8](=O)[CH:7]=2)CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].C([OH:26])C>O1CCCC1>[CH2:12]1[C@@H:13]2[N:9]([CH2:8][CH2:7][C:6](=[O:26])[CH2:14]2)[CH2:10][CH2:11]1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58681493(S)-7-(1-Pyrrolidinyl)-1,2,3,5,8,8a-hexahydroindolizin-5-one

Product 1

HCID 45087810(S)-1,2,3,5,6,7,8,8a-octahydroindolizin-7-oneYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-7-(1-Pyrrolidinyl)-1,2,3,5,8,8a-hexahydroindolizin-5-one (645 mg (3.13 mmol), prepared as described in 4)) was dissolved in tetrahydrofuran (10 ml). To the solution was added lithium aluminum hydride (356 mg, 9.39 mmol) under ice cooling, and the resulting mixture was stirred at room temperature overnight. To the reaction mixture were added an aqueous solution of 1N sodium hydroxide (1.44 ml) and ethanol, and insoluble material was filtered off. The filtrate was concentrated by distillation under reduced pressure and the resulting residue was purified by column chromatography through alumina (eluent, ethyl acetate), to give the title compound (236 mg) as a light brown oil (yield 54%).

Workup

  1. filtrationwas filtered off
  2. concentrationThe filtrate was concentrated by distillation under reduced pressure
  3. customthe resulting residue was purified by column chromatography through alumina (eluent, ethyl acetate)

Sources & evidence

ORD record
ord-6d722b272eb34204b63355ecb07a090c
Source dataset
uspto-grants-2006_08
Patent number
US07091352B2

Reaction notes

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