Sulfuric acid magnesium salt (1:1) → HCID 178519068, compound

HRID 908032Notes

Reaction equation

HRID 908032 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:13][CH2:12][CH2:11][N:10]2[C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[CH:5][CH:4]=1)=O.[NH2:24][C:25]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:26]=1[CH2:27][O:28][C:29]2=[O:34].[O-]S([O-])(=O)=O.[Mg+2]>CC#N>[O:34]=[C:29]1[C:30]2[C:26](=[C:25](/[N:24]=[CH:1]/[C:3]3[CH:4]=[CH:5][C:6]([CH:9]4[CH2:13][CH2:12][CH2:11][N:10]4[C:14]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:15])=[CH:7][CH:8]=3)[CH:33]=[CH:32][CH:31]=2)[CH2:27][O:28]1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 122846494-Amino-1,3-dihydro-2-benzofuran-1-oneHCID 86639042Benzyl 2-(4-formylphenyl)pyrrolidine-1-carboxylate

Product 1

HCID 178519068HCID 178519068, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of benzyl 2-(4-formylphenyl)pyrrolidine-1-carboxylate (0.62 g, 2 mmol), 4-aminoisobenzofuran-1(3H)-one (0.298 g, 2 mmol), MgSO4(2.4 g, 20 mmol) in CH3CN (20 mL) was refluxed at 120° C. for 4 days. After a hot filtration, the filtrate was concentrated in vacuo and the residue was purified by column chromatography (EtOAc:DCM:hexane=1:1:6) to give the title compound (0.35 g, yield 30%) as a white solid. LC-MS (ESI) m/z: 440 (M+1)+.

Workup

  1. filtrationAfter a hot filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customthe residue was purified by column chromatography (EtOAc:DCM:hexane=1:1:6)

Sources & evidence

ORD record
ord-3bfc54b02378450d8f8ae17f7d66277d
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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