Aluminium lithium hydride → 8-Phenyloctahydroindolizin-8-amine

HRID 1097627Notes

Reaction equation

HRID 1097627 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH2:7][C:8]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]2[N:12]([CH2:13][CH2:14][CH2:15]2)[C:11](=O)[CH2:10][CH2:9]1>C1COCC1>[C:18]1([C:8]2([NH2:7])[CH:16]3[N:12]([CH2:13][CH2:14][CH2:15]3)[CH2:11][CH2:10][CH2:9]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 585679118-Amino-8-phenyl-hexahydro-indolizin-5-one

Product 1

HCID 585679058-Phenyloctahydroindolizin-8-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 14 mg (0.33 mmol) LiAlH4 in 0.4 ml THF was added drop-wise a solution of 38 mg (0.165 mmol) (8R,S; 8aS,R)-8-amino-8-phenyl-hexahydro-indolizin-5-one in 0.4 ml THF at room temperature. The mixture was stirred at room temperature for 15 minutes and then refluxed for 30 minutes, cooled in an ice bath and quenched carefully with 15 ul water, 15 ul 5N NaOH and finally with 45 ul water. Ethyl acetate was added. The mixture was filtered and the filtrate was concentrated in vacuo to provide 30 mg (y: 84%) of the title compound as a colorless oil. (M+H+: 217.4).

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperaturecooled in an ice bath
  3. customquenched carefully with 15 ul water, 15 ul 5N NaOH and finally with 45 ul water
  4. additionEthyl acetate was added
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-04c6c42e5e12474db0795d967a71f70b
Source dataset
uspto-grants-2012_03
Patent number
US08143273B2

Reaction notes

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