Hydrochloric Acid → 2,5,7-Triazaspiro[3.4]octan-8-one--hydrogen chloride (1/1)

HRID 915850Notes

Reaction equation

HRID 915850 reaction equation
C([N:14]1[CH2:17][C:16]2([C:21](=[O:22])[N:20]=[CH:19][N:18]2CC2C=CC=CC=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:30]>CO.C(Cl)Cl.C(OCC)C>[ClH:30].[CH2:15]1[C:16]2([C:21](=[O:22])[NH:20][CH2:19][NH:18]2)[CH2:17][NH:14]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21905833HCID 21905833, compound

Product 1

HCID 534821002,5,7-Triazaspiro[3.4]octan-8-one--hydrogen chloride (1/1)

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 2-benzhydryl-5-benzyl-2,5,7-triazaspiro[3.4]oct-6-en-8-one (I-3A-50c; 1.83 g, 4.80 mmol) in methanol/methylene chloride was added excess 1 M HCl in diethyl ether (10 ml). After stirring for 10 minutes, the solvent was removed, in vacuo, and the resultant hydrochloride salt was dissolved in methanol (50 ml). After the addition of 20% Pd(OH)2 on carbon (50% water; 1.1 g), the mixture was placed on a Parr® shaker and then reduced (50 psi H2) at room temperature for 22 hours. The reaction was filtered through a 0.45 μM disk, and then concentrated, in vacuo, to give a gummy solid. This material was triturated from methanol to afford I-3A-50d (450 mg, 47%) as a tan solid: +APcl MS (M+1) 127.9; 1H NMR (400 MHz, CD3OD) δ 4.51 (s, 2H), 4.41-4.33 (m, 4H).

Workup

  1. customthe solvent was removed, in vacuo
  2. dissolutionthe resultant hydrochloride salt was dissolved in methanol (50 ml)
  3. additionAfter the addition of 20% Pd(OH)2 on carbon (50% water; 1.1 g)
  4. customat room temperature
  5. customfor 22 hours
  6. filtrationThe reaction was filtered through a 0.45 μM disk
  7. concentrationconcentrated, in vacuo
  8. customto give a gummy solid
  9. customThis material was triturated from methanol
  10. customto afford I-3A-50d (450 mg, 47%) as a tan solid

Sources & evidence

ORD record
ord-41115034870c44aab4fa8723b199dc3a
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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