Hydrochloric Acid → (7S)-5-Azaspiro[2.4]heptan-7-amine--hydrogen chloride (1/2)

HRID 324695Notes

Reaction equation

HRID 324695 reaction equation
C1([C@@H]([NH:9][C@H:10]2[C:14]3([CH2:16][CH2:15]3)[CH2:13][NH:12][CH2:11]2)C)C=CC=CC=1.C(O)C.[ClH:20].[H][H]>[OH-].[Pd+2].[OH-].O>[ClH:20].[ClH:20].[NH2:9][C@H:10]1[C:14]2([CH2:16][CH2:15]2)[CH2:13][NH:12][CH2:11]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 9920817(S)-7-[(S)-1-Phenylethyl]amino-5-azaspiro[2.4]heptaneHCID 178418361HCID 178418361, compound

Product 1

HCID 23539486(7S)-5-Azaspiro[2.4]heptan-7-amine--hydrogen chloride (1/2)Yield 82%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

Procedure

An autoclave was charged with 79 mg of (S)-7-[(S)-1-phenylethyl]amino-5-azaspiro[2.4]heptane, 37 mg of 20% palladium hydroxide, 2 ml of ethanol, 1 ml of water and 0.5 ml of concentrated hydrochloric acid, and the contents were stirred overnight at room temperature in an atmosphere of hydrogen (40 kgf/cm2). After completion of the reaction, the catalyst was removed by filtration and the resulting filtrate was concentrated under a reduced pressure to obtain 72 mg (82%) of the title compound in the form of colorless crystals. The thus obtained crystal compound was recrystallized from ethanol and diethyl ether and used as a sample for analyses.

Workup

  1. customAfter completion of the reaction
  2. customthe catalyst was removed by filtration
  3. concentrationthe resulting filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-251950c2e3284c4fabc0c09cdfbb6eef
Source dataset
uspto-grants-2001_04
Patent number
US06218548B1

Reaction notes

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