HCID 69416331, compound → HCID 69415611, compound

HRID 853061Notes

Reaction equation

HRID 853061 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:21][C@@H:20]([CH3:22])[N:11]2[C:12]3[CH:13]=[C:14](Br)[CH:15]=[CH:16][C:17]=3[CH2:18][C@@H:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cu][C:24]#[N:25]>O1CCOCC1.[C-]#N.C([N+](CC)(CC)CC)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:21][C@@H:20]([CH3:22])[N:11]2[C:12]3[CH:13]=[C:14]([C:24]#[N:25])[CH:15]=[CH:16][C:17]=3[CH2:18][C@@H:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 69416331HCID 69416331, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 69415611HCID 69415611, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 3014735Tetraethylammonium cyanideCatalystHCID 312751,4-DioxaneSolvent

Procedure

(4R,10aR)-7-Bromo-4-methyl-3,4,10,10a-tetrahydro-1H-pyrazino[1,2-a]indole-2-carboxylic acid tert-butyl ester (0.1 g) was dissolved in dioxane (2 mL) and copper(I)cyanide (0.1 g), tris-(dibenzylideneacetone)dipalladium chloroform complex (12 mg), 1,1′-bis(diphenylphosphino)ferrocene (24 mg) and tetraethylammonium cyanide (43 mg) were added. The mixture was heated to reflux for 18 h, cooled, filtered and the filter cake was washed with ethyl acetate. Saturated sodium bicarbonate solution (30 mL) was added to the filtrate, the phases were separated, the water phase was extracted with ethyl acetate (2-×20 mL) and the organic phases washed twice with saturated bicarbonate solution. Organic phases were pooled, dried with MgSO4 and the solvent removed in vacuo. Chromatography on silica gel (n-hexane/ethyl acetate 6:1) yielded the title compound as light yellow wax (34 mg; 40%). ISP-MS: m/e=314.2 (M+H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 h
  3. temperaturecooled
  4. filtrationfiltered
  5. washthe filter cake was washed with ethyl acetate
  6. additionSaturated sodium bicarbonate solution (30 mL) was added to the filtrate
  7. customthe phases were separated
  8. extractionthe water phase was extracted with ethyl acetate (2-×20 mL)
  9. washthe organic phases washed twice with saturated bicarbonate solution
  10. dry with materialdried with MgSO4
  11. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2a45a9af24484e8bb75f24586cfd703b
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

Loading…