HCID 86615013, compound → 5-(Cyclopropyl-hydroxymethyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester

HRID 732530Notes

Reaction equation

HRID 732530 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH2:6]([O:8][C:9](=[O:25])[C:10]1[CH:22]=[C:21]([CH:23]=[O:24])[CH:20]=[C:12]([C:13]([N:15]([CH3:19])[CH2:16][CH2:17][CH3:18])=[O:14])[CH:11]=1)[CH3:7]>C1COCC1>[CH2:6]([O:8][C:9](=[O:25])[C:10]1[CH:22]=[C:21]([CH:23]([CH:1]2[CH2:3][CH2:2]2)[OH:24])[CH:20]=[C:12]([C:13]([N:15]([CH3:19])[CH2:16][CH2:17][CH3:18])=[O:14])[CH:11]=1)[CH3:7]

Participants

4

Reactant 2

HCID 86615013HCID 86615013, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 688170545-(Cyclopropyl-hydroxymethyl)-N-methyl-N-propyl-isophthalamic acid ethyl esterYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Add cyclopropyl magnesium bromide (0.8 M in THF, 1.3 mL, 1.02 mmol) dropwise to a solution of 5-formyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (283 mg, 1.02 mmol) in THF (5 mL) at −10° C. After stirring at 0° C. for 1.5 h, quench the mixture with 5% aqueous ammonium chloride solution while maintaining the temperature below 5° C. Extract with ethyl acetate (3×30 mL), dry (sodium sulfate) concentrate and purify (silica gel chromatography, eluting with ethyl acetate and hexanes) to give the title compound (122 mg, 38%).

Workup

  1. customquench the mixture with 5% aqueous ammonium chloride solution
  2. temperaturewhile maintaining the temperature below 5° C
  3. extractionExtract with ethyl acetate (3×30 mL)
  4. dry with materialdry (sodium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-b35385df7dfb4e3b9fa83f75aaa2b798
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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