Water → HCID 86649761, compound

HRID 1640779Notes

Reaction equation

HRID 1640779 reaction equation
[CH2:1]([C@@:4]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[N:7]([C@H](C2C=CC(Br)=CC=2)C)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[OH2:26]>CN(C=O)C.Cl[Cu].Cl[Pd]Cl>[O:26]=[C:2]([CH3:3])[CH2:1][C:4]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:9][C:8](=[O:10])[NH:7][CH2:6][CH2:5]1

Participants

6

Reactant 2

HCID 962WaterHCID 59532360(R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one

Product 1

HCID 86649761HCID 86649761, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-6-allyl-3-((S)-1-(4-bromophenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (20 g, 50 mmol) and CuCl (12.4 g, 125 mmol) in dry DMF (50 mL) was added H2O (12 mL) and PdCl2 (2.66 g, 15 mmol) at 0˜−5° C. After addition, the mixture was allowed to warm to rt gradually for 48 h under O2. After TLC showing the stating material had disappeared, the solid was filtered off. Water (200 mL) and EtOAc (50 mL) were added. The layers were separated and the aqueous layer was extracted with EtOAc (3×40 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give a residue, which was purified by column chromatography to give (S)-3-(S)-1-(4-bromo-phenyl)ethyl)-6-(2-oxopropyl)-6-phenyl-1,3-oxazinan-2-one (12 g, 58%).

Workup

  1. additionAfter addition
  2. filtrationthe solid was filtered off
  3. additionWater (200 mL) and EtOAc (50 mL) were added
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (3×40 mL)
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a residue, which
  11. customwas purified by column chromatography

Sources & evidence

ORD record
ord-39a32985a14c4c568c311b480367859d
Source dataset
uspto-grants-2012_02
Patent number
US08114868B2

Reaction notes

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