N-methyl-2-pyrrolidone → HCID 86057584, compound

HRID 1821057Notes

Reaction equation

HRID 1821057 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH:12]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:11][CH2:10]2)(=O)=O.[CH3:23][N:24]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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.[Fe+2]>[C:23]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH:12]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:11][CH2:10]2)#[N:24]

Participants

6

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 131727668HCID 131727668, compound

Product 1

HCID 86057584HCID 86057584, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

To a solution methyl (R/S)-(5-trifluoromethylsulfonyloxy-indan-1-yl)acetate (2.63 g, 7.80 mmol, from Step D) in N-methylpyrrolidinone (20 mL) under argon, zinc cyanide (733 mg, 6.24 mmol), Pd2 dba3 (36 mg, 39.0 μmol) and dppf (52.0 mg, 93.6 μmol) were added, and the reaction mixture was heated to 100° C. After 16 hr, the reaction mixture was concentrated iji vacuo and partitioned between EtOAc and H2O. The layers were separated and the organic layer was washed with H2O, brine and dried over MgSO4. The mixture was filtered, the filtrate concentrated in vacuo, and the residue purified by flash chromatography (5, 10% EtOAc/hexanes) on SiO2 to give 1.40 g of the title compound as a white solid: 1H NMR (CDCl3) δ 1.80-1.84 (m, 1H), 2.43-2.48 (m, 1H), 2.52 (dd, 1H, J=8.5, 15.8 Hz), 2.77 (dd, 1H, J=6.0, 15.8 Hz), 2.92-3.00 (m, 2H), 3.62-3.66 (m, 1H), 3.74 (s, 3H), 7.27 (d, 1H, J=5.5 Hz), 7.47 (d, 1H, J=7.8 Hz), 7.51 (s, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated iji vacuo
  2. custompartitioned between EtOAc and H2O
  3. customThe layers were separated
  4. washthe organic layer was washed with H2O, brine
  5. dry with materialdried over MgSO4
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate concentrated in vacuo
  8. customthe residue purified by flash chromatography (5, 10% EtOAc/hexanes) on SiO2

Sources & evidence

ORD record
ord-7615c9cc196741f7b47c4f068d7e2f59
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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