Dimethylformamide → HCID 131726835, compound

HRID 901330Notes

Reaction equation

HRID 901330 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C@H:13]([C:27]([O:29][CH3:30])=[O:28])[CH2:14][C:15]1[CH:20]=[C:19](I)[CH:18]=[CH:17][C:16]=1[O:22][CH2:23][CH2:24][O:25][CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:31][N:32](C=O)C>C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C@H:13]([C:27]([O:29][CH3:30])=[O:28])[CH2:14][C:15]1[CH:20]=[C:19]([C:31]#[N:32])[CH:18]=[CH:17][C:16]=1[O:22][CH2:23][CH2:24][O:25][CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 70036013HCID 70036013, compound

Product 1

HCID 131726835HCID 131726835, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
73 °C

Procedure

2-(R)-{2-[5-Iodo-2-(2-methoxyethoxy)phenyl]-1-(R)-methyoxycarbonylethyl}pyrrolidine-1-carboxylic acid tert-butyl ester (0.25 g, 0.44 mmol) is dissolved in DMF (5 mL), degassed, and treated with tetrakis(triphenylphosphine) palladium zero (0.05 g, 0.044 mmol) and zinc cyanide (0.156 g, 1.33 mmol) under nitrogen. The reaction mixture is warmed to 73° C. for 2.5 h, cooled and diluted with ethyl acetate (100 mL). The resulting precipitate is removed and the filtrate is washed with water and brine and dried over MgSO4. The solvent is removed in vacuo and the residue is subjected to flash chromatography (ethyl acetate/hexane/methylene chloride: 1/2/1). The title compound is isolated a syrup (0.15 g, mmol). 1H NMR (CDCl3, 300 MHz) □ 7.50-7.38(m, 2H), 7.15(d, 1H), 5.31(s, 2H), 4.23-4.11(m, 1H), 3.83-3.76(m, 2H), 3.57(s, 3H), 3.56-3.48(m, 2H), 3.37(s, 3H), 3.36-3.26(m, 3H), 2.94-2.78(m, 1H), 2.76-2.61(m, 1H), 2.03-1.75(m, 4H), 1.45(s, 9H).

Workup

  1. customdegassed
  2. temperaturecooled
  3. customThe resulting precipitate is removed
  4. washthe filtrate is washed with water and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-930728ed4f10437f8e67d1ae40847fc4
Source dataset
uspto-grants-2008_04
Patent number
US07361663B2

Reaction notes

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