Water → 3-{2-[1-(6-Isobutyl-2-pyridyl)-4-piperidyl]ethyl}-1,3-oxazolidine-2,4-dione

HRID 1350583Notes

Reaction equation

HRID 1350583 reaction equation
Br[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]3[C:20](=[O:21])[CH2:19][O:18][C:17]3=[O:22])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.Br[Zn][CH2:25][CH:26]([CH3:28])[CH3:27].O.C(OCC)(=O)C>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:25]([C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]3[C:20](=[O:21])[CH2:19][O:18][C:17]3=[O:22])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1)[CH:26]([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 210969643-{2-[1-(6-Bromo-2-pyridyl)-4-piperidyl]ethyl}-1,3-oxazolidine-2,4-dioneHCID 178448255HCID 178448255, compound

Product 1

HCID 210969683-{2-[1-(6-Isobutyl-2-pyridyl)-4-piperidyl]ethyl}-1,3-oxazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

2 g (5.43 mmol) of 3-{2-[1-(6-bromo-2-pyridyl)-4-piperidyl]ethyl}-1,3-oxazolidine-2,4-dione, prepared in step 13.3, and 0.20 g (0.271 mmol) of dichlorobis(triphenylphosphine)palladium (Pd(PPh3)2Cl2) suspended in 10 ml of tetrahydrofuran are introduced under an inert atmosphere. 22 ml (10.80 mmol) of a solution (0.5 M) of bromo(isobutyl)zinc in tetrahydrofuran are then added. Stirring is continued at room temperature for 17 hours. The reaction mixture is poured into water and ethyl acetate. The phases are separated by settling, the aqueous phase is extracted twice with ethyl acetate, the combined organic phases are dried over sodium sulfate and the filtrate is concentrated under reduced pressure. The residue thus obtained is purified by chromatography on silica gel, eluting with a 20/80 mixture of ethyl acetate and cyclohexane.

Workup

  1. additionare introduced under an inert atmosphere
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted twice with ethyl acetate
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe residue thus obtained
  7. customis purified by chromatography on silica gel
  8. washeluting with a 20/80 mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-02ef537c64c14fe082d3db63e50c1fec
Source dataset
uspto-grants-2007_05
Patent number
US07214798B2

Reaction notes

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