Tetrahydrofuran → (S)-7-[(S)-1-Phenylethyl]amino-5-azaspiro[2.4]heptane

HRID 849672Notes

Reaction equation

HRID 849672 reaction equation
[C:1]1([C@@H:7]([NH:9][C@H:10]2[C:14]3([CH2:16][CH2:15]3)[C:13](=O)[NH:12][CH2:11]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1>[H-].[Al+3].[Li+].[H-].[H-].[H-]>[C:1]1([C@@H:7]([NH:9][C@H:10]2[C:14]3([CH2:16][CH2:15]3)[CH2:13][NH:12][CH2:11]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 9794602HCID 9794602, compound

Product 1

HCID 9920817(S)-7-[(S)-1-Phenylethyl]amino-5-azaspiro[2.4]heptane

Reagents, catalysts & solvents 1

HCID 21226445Aluminium lithium hydrideSolvent

Procedure

A flask was charged with 200 mg of (S)-7-[(S)-1-phenylethyl]amino-4-oxo-5-azaspiro[2.4]heptane, and the atmosphere in the flask was replaced with nitrogen. Next, 5 ml of tetrahydrofuran was added to dissolve the compound in the flask, 5.0 ml of lithium aluminum hydride (1 M solution in tetrahydrofuran) was added dropwise to the resulting solution at 0° C. and then the mixture was heated under reflux for 1 hour. After confirming completion of the reaction, the reaction was terminated by adding saturated ammonium chloride solution and then the insoluble matter was removed by filtration. The resulting filtrate was concentrated under a reduced pressure and distributed between ethyl acetate and saturated brine, and the resulting organic layer was dried over anhydrous sodium sulfate. Thereafter, the insoluble matter was removed by filtration and the resulting filtrate was concentrated under a reduced pressure to obtain 181 mg (96%) of colorless oily substance.

Workup

  1. additionwas added dropwise to the resulting solution at 0° C.
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. customcompletion of the reaction
  5. customthe reaction was terminated
  6. additionby adding saturated ammonium chloride solution
  7. customthe insoluble matter was removed by filtration
  8. concentrationThe resulting filtrate was concentrated under a reduced pressure
  9. dry with materialthe resulting organic layer was dried over anhydrous sodium sulfate
  10. customThereafter, the insoluble matter was removed by filtration
  11. concentrationthe resulting filtrate was concentrated under a reduced pressure
  12. customto obtain 181 mg (96%) of colorless oily substance

Sources & evidence

ORD record
ord-94bfd77a49174e5592891f068f2fef80
Source dataset
uspto-grants-2000_01
Patent number
US06013806

Reaction notes

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