N-methyl-2-pyrrolidone → HCID 66922282, compound

HRID 2039847Notes

Reaction equation

HRID 2039847 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:24]3[C:19](=[C:20](Cl)[N:21]=[CH:22][CH:23]=3)[N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]=2[O:32][C:33]2[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=2[CH3:40])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1C(=O)C[CH2:44][CH2:43]1.C([Mg]Cl)C>C1COCC1.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:24]3[C:19](=[C:20]([CH2:43][CH3:44])[N:21]=[CH:22][CH:23]=3)[N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]=2[O:32][C:33]2[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=2[CH3:40])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 87206049HCID 87206049, compoundHCID 178461633HCID 178461633, compound

Product 1

HCID 66922282HCID 66922282, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 5483663Ferric acetylacetonateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of the compound of example 38, step 6, (65 mg, 115 μmol), iron(III) acetylacetonate (2.03 mg, 5.7 μmol) and NMP (102.6 mg, 1.04 mmol) in THF (5 ml) was cooled to 0° C. Ethylmagnesium chloride (115 μl, 230 μmol, 2 M in THF) was added and the resulting solution was stirred for 5 min. The brown mixture was quenched with water and extracted with EA. The organic layers were dried over sodium sulfate and concentrated. The residue was purified by silica gel chromatography (EA/HEP) to give 29 mg of the title compound.

Workup

  1. customThe brown mixture was quenched with water
  2. extractionextracted with EA
  3. dry with materialThe organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (EA/HEP)

Sources & evidence

ORD record
ord-bfdbefa18c9640b9a4d6bb47fc813607
Source dataset
uspto-grants-2013_11
Patent number
US08580813B2

Reaction notes

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