Dimethylformamide → HCID 53901059, compound

HRID 1708596Notes

Reaction equation

HRID 1708596 reaction equation
[CH:1]1([N:7]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12](Br)=[C:11]([CH3:16])[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])(C)(C)C.CN(C)[CH:30]=[O:31]>C1COCC1>[CH:1]1([N:7]([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([CH:30]=[O:31])=[C:11]([CH3:16])[CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 19754882HCID 19754882, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 53901059HCID 53901059, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (-70° C.), stirred solution of 4-bromo-3-methylbenzoic acid N-cyclohexyl-N-cyclopentyl amide (4 g, 0.011 mol) in THF (40 mL) was added t-butyl lithium (13 mL of 1.7 M solution) via syringe over 10 min. The originally colorless solution became a dark red. Dimethylformamide (DMF) (884 mg) was added. The cold bath was removed and the reaction allowed to warm to 0° , during the course of which, the reaction became much lighter in color. The reaction was diluted with ethyl acetate, washed with 0.5 N KHSO4 and the organic layer was dried (Na2SO4). The drying agent was filtered, the filtrate concentrated in vacuo and the crude product purified by chromatography on silica gel using mixtures of ethyl acetate and hexane as eluents to give title compound of Step(a), m.p. 57°-59° C. Anal. Calcd for C20H27NO2 : C, 76.64; H, 8.68; N, 4.47. Found: C, 76.21; H, 8.71; N, 4.11.

Workup

  1. customThe cold bath was removed
  2. temperatureto warm to 0° , during the course of which
  3. additionThe reaction was diluted with ethyl acetate
  4. washwashed with 0.5 N KHSO4
  5. dry with materialthe organic layer was dried (Na2SO4)
  6. filtrationThe drying agent was filtered
  7. concentrationthe filtrate concentrated in vacuo
  8. customthe crude product purified by chromatography on silica gel using mixtures of ethyl acetate and hexane as eluents

Sources & evidence

ORD record
ord-e20e4e8409aa4148bbcfedbd404ebcdb
Source dataset
uspto-grants-1994_10
Patent number
US05359073

Reaction notes

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