Tributylvinyltin → HCID 68692187, compound

HRID 1296317Notes

Reaction equation

HRID 1296317 reaction equation
[CH2:1]([N:8]1[CH2:23][CH2:22][N:11]2[C:12](=[O:21])[C:13]3[CH:14]=[C:15]([CH3:20])[CH:16]=[CH:17][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.[CH2:24]([Sn](CCCC)(CCCC)C=C)CCC.[Li+].[Cl-]>C1(C)C=CC=CC=1.C(OCC)(=O)C.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>[CH2:1]([N:8]1[CH2:23][CH2:22][N:11]2[C:12](=[O:21])[C:13]3[CH:14]=[C:15]([CH:20]=[CH2:24])[CH:16]=[CH:17][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

7

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 68690914HCID 68690914, compound

Product 1

HCID 68692187HCID 68692187, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Degassed mixture of (R)-2-Benzyl-8-methyl-1,2,3,4,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-6-one (50 mg, 0.13 mmol), tributyl(vinyl)tin (64 mg, 0.20 mmol), dichlorobis(triphenylphosphine)palladium (9.1 mg, 0.013 mmol) and LiCl (27.5 mg, 0.65 mmol) in toluene (1 mL) was heated at 110° C. for 18 h to give dark brownish reaction mixture. The mixture was then cooled, diluted with ethyl acetate(10 mL) and filtered through bed of celite and rinsed with more ethyl acetate(20 mL). Filtrate was concentrated and purified by prep TLC (SiO2, 95:5, CH2Cl2:MeOH) to give (25 mg, 60%) as a faint yellow oil. MS (ESI) 319 (M+H).

Workup

  1. customDegassed
  2. customto give dark
  3. custombrownish reaction mixture
  4. temperatureThe mixture was then cooled
  5. filtrationfiltered through bed of celite and
  6. washrinsed with more ethyl acetate(20 mL)
  7. concentrationFiltrate was concentrated
  8. custompurified by prep TLC (SiO2, 95:5, CH2Cl2:MeOH)
  9. customto give (25 mg, 60%) as a faint yellow oil

Sources & evidence

ORD record
ord-06fd3cc6bdb446afbe53940e30406ffc
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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