HCID 57215384, compound → HCID 57003213, compound

HRID 2296659Notes

Reaction equation

HRID 2296659 reaction equation
C([O:8][CH2:9][C@H:10]1[C@H:15]([CH3:16])[N:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][CH2:12][N:11]1[S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)(=[O:23])=[O:22])C1C=CC=CC=1>O1CCOCC1.CO.[H][H].[OH-].[Pd+2].[OH-]>[OH:8][CH2:9][C@H:10]1[C@H:15]([CH3:16])[N:14]([S:17]([CH3:20])(=[O:18])=[O:19])[CH2:13][CH2:12][N:11]1[S:21]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=1)(=[O:22])=[O:23]

Participants

6

Reactant 1

HCID 57215384HCID 57215384, compound

Product 1

HCID 57003213HCID 57003213, compoundYield 94.9%

Reagents, catalysts & solvents 4

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

A mixture of (2R,3S)-2-benzyloxymethyl-4-methanesulfonyl-1-(4-methoxybenzenesulfonyl)-3-methylpiperazine (330 mg) and palladium hydroxide (40 mg) in dioxane (5 ml) and MeOH (5 ml) was hydrogenated in hydrogen at 3.5 atm and ambient temperature for 1 day. The catalyst was removed by filtration through a celite pad and the pad was washed with MeOH. The filtrate and combined washings were concentrated in vacuo. The residue was purified by SiO2 column chromatography (eluent: AcOEt/n-hexane 60%, then MeOH/AcOEt 1%) to give 253 mg of (2R,3S)-2-hydroxymethyl-4-methanesulfonyl-1-(4-methoxybenzenesulfonyl)-3-methylpiperazine.

Workup

  1. customThe catalyst was removed by filtration through a celite pad
  2. washthe pad was washed with MeOH
  3. concentrationwere concentrated in vacuo
  4. customThe residue was purified by SiO2 column chromatography (eluent

Sources & evidence

ORD record
ord-1c21a190d0a24acbbaa55c181bdaa9ef
Source dataset
uspto-grants-2002_12
Patent number
US06489324B2

Reaction notes

Loading…