Triethylamine → Methyl 3-{[isopentyl(methyl)amino]methyl}-5-methylbenzoate

HRID 14153Notes

Reaction equation

HRID 14153 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].CS(Cl)(=O)=O.C(N(CC)CC)C.[CH3:26][NH:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31]>C(Cl)Cl>[CH2:28]([N:27]([CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([CH3:13])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])[CH3:26])[CH2:29][CH:30]([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 521020N,3-Dimethyl-1-butanamineHCID 21086184Methyl 3-(hydroxymethyl)-5-methylbenzoate

Product 1

HCID 21086187Methyl 3-{[isopentyl(methyl)amino]methyl}-5-methylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To methyl 3-(hydroxymethyl)-5-methylbenzoate prepared by the method in Example SP-198, Step 2 in anhydrous methylene chloride at −30° C. is added methanesulfonyl chloride (601 μL, 7.8 mmol), then triethylamine (1.5 mL, 11.1 mmol), and the reaction is stirred at 0° C. 15 min. The resulting precipitate is filtered, and the filtrate is added to N-methylisoamylamine (2.1 mL, 16.7 mmol). The reaction stirred at room temperature 16 h. The solution is concentrated under reduced pressure, redissolved in ethyl acetate and washed with saturated sodium bicarbonate, brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 20% ethyl acetate/hexanes) provides the title compound. ESI MS m/z 264.2 [M+H]+.

Workup

  1. custom15 min
  2. filtrationThe resulting precipitate is filtered
  3. concentrationThe solution is concentrated under reduced pressure
  4. dissolutionredissolved in ethyl acetate
  5. washwashed with saturated sodium bicarbonate, brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash column chromatography (silica, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-00113c35734347b0be9a174aae6a904f
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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