HCID 67051897, compound → HCID 67051836, compound

HRID 1672972Notes

Reaction equation

HRID 1672972 reaction equation
C1(C[N:8]2[CH2:13][CH2:12][N:11](CC3C=CC=CC=3)[CH2:10][CH:9]2[C:21]2([OH:32])[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22]2)C=CC=CC=1.[H][H]>CO.[Pd]>[OH:32][C:21]1([CH:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)[CH2:22][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24]1

Participants

5

Reactant 2

HCID 67051897HCID 67051897, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67051836HCID 67051836, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl 3-[1,4-bis(phenylmethyl)piperazin-2-yl]-3-hydroxyazetidine-1-carboxylate (408 mg, 0.93 mmol) in methanol (15 mL) was added 10% palladium on carbon (wet), and the resulting suspension was subjected to an atmosphere of hydrogen for 21 hours. The catalyst was removed by filtration through celite, and the filter cake was rinsed with methanol. The combined filtrate was concentrated to provide 1,1-dimethylethyl 3-hydroxy-3-piperazin-2-ylazetidine-1-carboxylate as a brown syrup (227 mg, 0.88 mmol, 95% yield). 1H NMR (400 MHz, CDCl3): 3.94-3.76 (m, 5H), 3.12 (m, 1H), 3.01 (m, 1H), 2.94-2.81 (m, 3H), 2.78-2.70 (m, 2H); MS (EI) for C12H23N3O3: 258 (MH+).

Workup

  1. customThe catalyst was removed by filtration through celite
  2. washthe filter cake was rinsed with methanol
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-5509eae68f59440398b6b88eb065995f
Source dataset
uspto-grants-2011_08
Patent number
US07999006B2

Reaction notes

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