Methanol → HCID 69358385, compound

HRID 852647Notes

Reaction equation

HRID 852647 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:12]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:10]=[C:6]([C:7](O)=[O:8])[CH:5]=1.CO>C1COCC1>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:12]=[C:11]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:10]=[C:6]([CH2:7][OH:8])[CH:5]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 69358928HCID 69358928, compound

Product 1

HCID 69358385HCID 69358385, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 5-(2-oxo-pyrrolidin-1-yl)-isophthalic acid monomethyl ester (A75) (200 mg, 0.76 mmol, 1 equiv) in THF (20 ml) was cooled to 0° C. and treated with BH3-Me2S (2M solution in THF, 0.64 ml, 1.28 mmol, 1.3 equiv). The resulting mixture was refluxed for 1 h and then cooled to room temperature. MeOH (5 ml) was added and the resulting mixture was concentrated in vacuo. The residue was diluted with AcOEt (50 ml) and the resulting solution was washed with saturated aqueous NaHCO3 solution (30 ml) and 2N aqueous HCl solution (30 ml), dried over MgSO4 and concentrated in vacuo to give 3-hydroxymethyl-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (B76) (70 mg, 37%) as a pale yellow oil.

Workup

  1. temperatureThe resulting mixture was refluxed for 1 h
  2. temperaturecooled to room temperature
  3. concentrationthe resulting mixture was concentrated in vacuo
  4. additionThe residue was diluted with AcOEt (50 ml)
  5. washthe resulting solution was washed with saturated aqueous NaHCO3 solution (30 ml) and 2N aqueous HCl solution (30 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8250ec872b34a61ad9c817b1f5961ef
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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