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Hydrochloric Acid → 5-Azaspiro[2.4]heptan-7-ol hydrochloride

HRID 1366496
Notes
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Reaction equation

HRID 1366496 reaction equation
C1(C[N:8]2[CH2:14][CH:13]([OH:15])[C:10]3([CH2:12][CH2:11]3)[CH2:9]2)C=CC=CC=1.[ClH:16]>CO>[ClH:16].[CH2:11]1[C:10]2([CH:13]([OH:15])[CH2:14][NH:8][CH2:9]2)[CH2:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 584529235-Benzyl-5-azaspiro[2.4]heptan-7-ol

Product 1

HCID 669359925-Azaspiro[2.4]heptan-7-ol hydrochlorideYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(Phenylmethyl)-5-azaspiro[2.4]heptan-7-ol (assumed 941.9 mg, 4.63 mmol) was dissolved in a solution of 4.6 mL of 1N aq HCl in 40 mL of MeOH, degassed and placed under argon. 10% Pd/C (280 mg) was added, and the contents were thoroughly degassed and placed under a hydrogen balloon overnight. The contents were then degassed and filtered through Celite, and the Celite pad was washed with MeOH. The resulting filtrate was concentrated in vacuo and azeotroped with MeOH (3×40 mL) to provide the pure 5-azaspiro[2.4]heptan-7-ol hydrochloride (685 mg, 99%). LCMS: (M+H)+: not detected.

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Workup

  1. customdegassed
  2. addition10% Pd/C (280 mg) was added
  3. customthe contents were thoroughly degassed
  4. customballoon overnight
  5. customThe contents were then degassed
  6. filtrationfiltered through Celite
  7. washthe Celite pad was washed with MeOH
  8. concentrationThe resulting filtrate was concentrated in vacuo
  9. customazeotroped with MeOH (3×40 mL)

Sources & evidence

ORD record
ord-1308249cba8b48dd96002798cd011088
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07893056B2

Reaction notes

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