Acetonitrile → HCID 57425696, compound

HRID 1360120Notes

Reaction equation

HRID 1360120 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=O.[NH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.[Br:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.[C:22](#N)C>>[Br:12][C:13]1[CH:14]=[C:15]([CH:3]([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[C:2]([O:6][CH3:22])=[O:5])[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 31268PyrrolidineHCID 2734318(3-Bromophenyl)boronic acidHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 57425696HCID 57425696, compound

Procedure

To a mixture of glyoxylic acid monohydrate (1.54 g), pyrrolidine (1.19 g), and 220 mL acetonitrile was added 3-bromophenyl boronic acid (3.35 g). The reaction was heated at 80 C for 93 h. After cooling to room temperature, volatiles were removed in vacuo, and the residue was dissolved in 75 mL of benzene and 38 mL of methanol. Trimethylsilyldiazomethane (2M in hexanes, 16.7 mL) was added via syringe, and the reaction was stirred at room temperature for 2.5 h. The volatiles were removed in vacuo, and the residue was purified by flash chromatography to provide 1.53 g of methyl (3-bromophenyl)(pyrrolidin-1-yl)acetate. MS 298, 300 (Br).

Workup

  1. temperatureThe reaction was heated at 80 C for 93 h
  2. customvolatiles were removed in vacuo
  3. dissolutionthe residue was dissolved in 75 mL of benzene
  4. additionTrimethylsilyldiazomethane (2M in hexanes, 16.7 mL) was added via syringe
  5. customThe volatiles were removed in vacuo
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5a9929e02c724a97aef536dbd06cd6ec
Source dataset
uspto-grants-2011_02
Patent number
US07879839B2

Reaction notes

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