Toluene → HCID 68686462, compound

HRID 1159109Notes

Reaction equation

HRID 1159109 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12](=[O:14])[NH:11][C@H:10]([CH2:15][C:16]2[CH:21]=[C:20](Br)[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1(C)C=CC=CC=1>O1CCOCC1.C[Zn]C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([N:8]1[CH2:13][C:12](=[O:14])[NH:11][C@H:10]([CH2:15][C:16]2[CH:21]=[C:20]([CH3:26])[CH:19]=[CH:18][C:17]=2[O:23][CH3:24])[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 1140TolueneHCID 68689925HCID 68689925, compound

Product 1

HCID 68686462HCID 68686462, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolventHCID 178477796HCID 178477796, compoundSolvent

Procedure

To a degassed mixture of (R)-1-benzyl-3-(5-bromo-2-methoxy-benzyl)-piperazine-2,5-dione (1.91 g, 4.74 mmol) and Pd(dppf)Cl2 (0.12 g, 0.14 mmol) in dioxane (18 mL), 2M dimethyl zinc in toluene (4.74 mL, 9.48 mmol) was slowly added at 0° C. and heated at reflux for 1 h to give dark brownish reaction mixture. The mixture was then cooled RT and quenched with methanol (10 mL) and filtered off the precipitate and rinsed with more methanol (20 mL). Filtrate was concentrated and purified (SiO2, 95:5, CH2Cl2:MeOH) to give (1.33 g, 83%) as a amber oil. MS (ESI) 339 (M+H).

Workup

  1. additionwas slowly added at 0° C.
  2. temperatureheated
  3. temperatureat reflux for 1 h
  4. customto give dark
  5. custombrownish reaction mixture
  6. customquenched with methanol (10 mL)
  7. filtrationfiltered off the precipitate
  8. washrinsed with more methanol (20 mL)
  9. concentrationFiltrate was concentrated
  10. custompurified (SiO2, 95:5, CH2Cl2:MeOH)
  11. customto give (1.33 g, 83%) as a amber oil

Sources & evidence

ORD record
ord-b42373948ea7499e920210cf311834a6
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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