Ethanol → HCID 57457957, compound

HRID 1245038Notes

Reaction equation

HRID 1245038 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][CH:8]1[C@H:16]2[N:12]([CH2:13][CH2:14][CH2:15]2)[C:11](=O)[CH:10]=[C:9]1N1CCCC1.[OH-].[Na+].C([OH:27])C>O1CCCC1>[CH3:7][CH:8]1[C@H:16]2[N:12]([CH2:13][CH2:14][CH2:15]2)[CH2:11][CH2:10][C:9]1=[O:27]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57501858HCID 57501858, compound

Product 1

HCID 57457957HCID 57457957, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.79 g (47.1 mmol) of lithium aluminum hydride were added in several portions to a stirred, ice-cooled solution of 3.67 g (15.7 mmol) of (8aS)-8-methyl-7-(1-pyrrolidinyl)-1,2,3,5,8,8a-hexahydroindolizin-5-one [obtained as described in Preparative Example 9(iv)′ above] in 50 ml of tetrahydrofuran and the resulting mixture was stirred at room temperature overnight. At the end of this time, 7.22 ml of a 1N aqueous solution of sodium hydroxide were added followed by the addition of ethanol, and any insoluble material was then filtered off. The filtrate thus obtained was concentrated by evaporation under reduced pressure, and the resulting residue was purified by chromatography on an alumina column using ethyl acetate as the eluant to afford 1.69 g (yield: 70%) of the title compound as a pale yellow oil.

Workup

  1. customobtained
  2. filtrationany insoluble material was then filtered off
  3. customThe filtrate thus obtained
  4. concentrationwas concentrated by evaporation under reduced pressure
  5. customthe resulting residue was purified by chromatography on an alumina column

Sources & evidence

ORD record
ord-5e0ccb318d1d46df91292f944ef4d6b1
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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