HCID 57979768, compound → HCID 57979779, compound

HRID 1868029Notes

Reaction equation

HRID 1868029 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C@@H:19]([CH3:20])[CH2:18][N:17](C(OCC3C=CC=CC=3)=O)[CH2:16][C@@H:15]2[CH3:31])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]2[C@@H:19]([CH3:20])[CH2:18][NH:17][CH2:16][C@@H:15]2[CH3:31])(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 57979768HCID 57979768, compound

Product 1

HCID 57979779HCID 57979779, compoundYield 53.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of benzyl (3S,5S)-4-[(4-tert-butylphenyl)sulfonyl]-3,5-dimethylpiperazine-1-carboxylate (340 mg, 0.77 mmol) in anhydrous MeOH was hydrogenated at 1 atmosphere for 2 days using palladium, 10% wt. on activated carbon (144 mg) as catalyst. Reaction was complete as determined by TLC. The reaction mixture was then filtered through a celite bed. After solvent evaporation crude product was purified via flash column chromatography to afford (2S,6S)-1-[(4-tert-butylphenyl)sulfonyl]-2,6-dimethylpiperazine in 53.9% yield (128 mg) as pale yellow oil.

Workup

  1. customReaction
  2. filtrationThe reaction mixture was then filtered through a celite bed
  3. customAfter solvent evaporation crude product
  4. customwas purified via flash column chromatography

Sources & evidence

ORD record
ord-480e1a015de34637be8d8817135f4c55
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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