Sulfuric acid magnesium salt (1:1) → 4-(2-{2-[(2R)-2-methyl-5-oxo-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile

HRID 494878Notes

Reaction equation

HRID 494878 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)=[CH:14][C:12]=2[CH:13]=1.[O-:26][Mn](=O)(=O)=O.[K+].[O-]S([O-])(=O)=O.[Mg+2]>CC(C)=O.O>[CH3:1][C@@H:2]1[CH2:6][CH2:5][C:4](=[O:26])[N:3]1[CH2:7][CH2:8][C:9]1[O:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[CH:20][C:21]([C:22]#[N:23])=[CH:24][CH:25]=3)=[CH:14][C:12]=2[CH:13]=1

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 9818903Benzonitrile, 4-(2-(2-((2r)-2-methyl-1-pyrrolidinyl)ethyl)-5-benzofuranyl)-

Product 1

HCID 675340094-(2-{2-[(2R)-2-methyl-5-oxo-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrileYield 2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

The mono-(L)-tartaric acid salt of the product of Example 1D (96 mg, 0.20 mmol) was suspended in acetone (10 mL) and treated with a solution of KMnO4 (158 mg, 1.0 mmol) and MgSO4 (120 mg, 1.0 mmol) in water (5 mL) over 30 minutes. After the purple color had disappeared, the solids were filtered off. The filtrate was diluted with EtOAc, washed with aqueous potassium dihydrogen phosphate, concentrated, and purified by HPLC [Waters Nova-Pak HR C18 column (25 mm×100 mm, 6 μm particle size) using a gradient of 10% to 100% MeCN/0.1% aqueous TFA over 8 min (10 min run time) at a flow rate of 40 mL/min.] to provide the title compound (2% yield). MS (ESI APCI) m/z 345 (M+H)+; 1HNMR (300 MHz, CD3OD) δ 1.22 (d, 3H), 1.55-1.64 (m, 1H), 2.15-2.32 (m, 2H), 2.34-2.42 (m, 1H), 2.99-3.13 (m, 2H), 3.39-3.46 (m, 1H), 3.68-3.76 (m, 1H), 3.89-3.97 (m, 1H), 6.65 (s, 1H), 7.51-7.56 (m, 2H), 7.76-7.84 (m, 5H).

Workup

  1. filtrationthe solids were filtered off
  2. additionThe filtrate was diluted with EtOAc
  3. washwashed with aqueous potassium dihydrogen phosphate
  4. concentrationconcentrated
  5. custompurified by HPLC [Waters Nova-Pak HR C18 column (25 mm×100 mm, 6 μm particle size)
  6. customover 8 min
  7. custom(10 min run time)

Sources & evidence

ORD record
ord-8f33f461fed5498f81ed394c6575e4b4
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

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