Toluene → HCID 68689746, compound

HRID 1159112Notes

Reaction equation

HRID 1159112 reaction equation
[CH2:1]([N:8]1[CH2:25][CH2:24][N:11]2[C:12](=[O:23])[C:13]3[C:14]([CH3:22])=[CH:15][C:16](Br)=[C:17]([OH:20])[C:18]=3[CH2:19][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26]1(C)C=CC=C[CH:27]=1>O1CCOCC1.C([Zn]CC)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[CH2:25][CH2:24][N:11]2[C:12](=[O:23])[C:13]3[C:14]([CH3:22])=[CH:15][C:16]([CH2:26][CH3:27])=[C:17]([OH:20])[C:18]=3[CH2:19][C@@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 1140TolueneHCID 68689713HCID 68689713, compound

Product 1

HCID 68689746HCID 68689746, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolventHCID 178418750HCID 178418750, compoundSolvent

Procedure

To a degassed mixture of (R)-2-benzyl-7-methyl-9-bromo-10-hydroxy-1,2,3,4,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-6-one (45 mg, 0.11 mmol) and Pd(dppf)Cl2 (0.12 g, 0.14 mmol) in dioxane (1.25 mL), 1.1M diethyl zinc in toluene (0.21 mL, 0.22 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 on prep TLC (SiO2, 95:5, CH2Cl2:MeOH) to give (50 mg, 93%) as a faint yellow oil. MS (ESI) 351 (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 on prep TLC (SiO2, 95:5, CH2Cl2:MeOH)
  11. customto give (50 mg, 93%) as a faint yellow oil

Sources & evidence

ORD record
ord-e88ff37afe24449c96da32c9e9d77ff5
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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