Hydrochloric Acid → 5-Methyl-2,5,7-triazaspiro[3.4]octan-8-one

HRID 915846Notes

Reaction equation

HRID 915846 reaction equation
C([N:14]1[CH2:17][C:16]2([C:21](=[O:22])[N:20]=[CH:19][N:18]2[CH3:23])[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:24]>CO.C(OCC)C.[OH-].[OH-].[Pd+2]>[ClH:24].[CH3:23][N:18]1[CH2:19][NH:20][C:21](=[O:22])[C:16]21[CH2:17][NH:14][CH2:15]2

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 21905771HCID 21905771, compound

Product 1

HCID 1317260095-Methyl-2,5,7-triazaspiro[3.4]octan-8-one

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2-benzhydryl-5-methyl-2,5,7-triazaspiro[3.4]oct-6-en-8-one (I-2A-69c; 189 mg, 0.619 mmol) in methanol (30 ml) was added 1 M HCl in diethyl ether (1.3 ml). After the addition of 20% Pd(OH)2 on carbon (50% water; 95 mg), the mixture was placed on a Parr® shaker and then reduced (50 psi H2) at room temperature for 5 hours. The reaction mixture was filtered through a 0.45 PM disk, and then concentrated, in vacuo, to give a solid. Trituration from diethyl ether afforded I-2A-69d (124 mg, 94%) as an off-white solid: +APcl MS (M+1) 142.0; 1H NMR (400 MHz, CD3OD) δ 4.38 (d, J=12.0 Hz, 2H), 4.17 (s, 2H), 4.13 (d, J=12.5 Hz, 2H), 2.71 (s, 3H).

Workup

  1. customat room temperature
  2. customfor 5 hours
  3. filtrationThe reaction mixture was filtered through a 0.45 PM disk
  4. concentrationconcentrated, in vacuo
  5. customto give a solid

Sources & evidence

ORD record
ord-d86ad0b1d42248f281bd39a505b6b983
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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