Water → Pyrrolidine-1,2-dicarboxylic acid 2-{2-[7-(2-bromo-acetyl)-dibenzofuran-3-yl]-2-oxo-ethyl}ester 1-tert-butyl ester

HRID 79855Notes

Reaction equation

HRID 79855 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH2:16][C:17]([C:19]1[CH:20]=[CH:21][C:22]2[C:26]3[CH:27]=[CH:28][C:29](Br)=[CH:30][C:25]=3[O:24][C:23]=2[CH:32]=1)=[O:18])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[CH:38]=[CH:39][O:40]CC)CCC.O.C1C(=O)N([Br:59])C(=O)C1>O1CCOCC1.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>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH2:16][C:17]([C:19]1[CH:20]=[CH:21][C:22]2[C:26]3[CH:27]=[CH:28][C:29]([C:39](=[O:40])[CH2:38][Br:59])=[CH:30][C:25]=3[O:24][C:23]=2[CH:32]=1)=[O:18])=[O:14])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)etheneHCID 66621169Pyrrolidine-1,2-dicarboxylic acid 2-[2-(7-bromo-dibenzofuran-3-yl)-2-oxo-ethyl] ester 1-tert-butyl ester

Product 1

HCID 72338318Pyrrolidine-1,2-dicarboxylic acid 2-{2-[7-(2-bromo-acetyl)-dibenzofuran-3-yl]-2-oxo-ethyl}ester 1-tert-butyl esterYield 75.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To the solution of Pyrrolidine-1,2-dicarboxylic acid 2-[2-(7-bromo-dibenzofuran-3-yl)-2-oxo-ethyl] ester 1-tert-butyl ester (250 mg, 0.5 mmol) and tributyl(ethoxyvinyl)stannane (188 μl, 0.55 mmol) in dioxane (3.3 ml) was added PdCl2(PPh3)2 (15 mg). The mixture was heated at 80° C. for 16 hours and was cooled to 0° C. Water (1.1 ml) was added, followed by slow addition of NBS (98 mg, 0.55 mmol) over 5 minutes period. The mixture was stirred at 0° C. for additional 40 minutes, and the solvent was removed under reduced pressure. The mixture was diluted with EtOAc, and was washed with water and brine and dried with sodium sulfate. Concentration and purification by flash column chromatography (hexane/EtOAc) gave Pyrrolidine-1,2-dicarboxylic acid 2-{2-[7-(2-bromo-acetyl)-dibenzofuran-3-yl]-2-oxo-ethyl}ester 1-tert-butyl ester (205 mg).

Workup

  1. temperaturewas cooled to 0° C
  2. customthe solvent was removed under reduced pressure
  3. additionThe mixture was diluted with EtOAc
  4. washwas washed with water and brine
  5. dry with materialdried with sodium sulfate
  6. concentrationConcentration and purification by flash column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-23c521f60bf94ca7b8e16456d9b444df
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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