Methanol → HCID 59570148, compound

HRID 2071143Notes

Reaction equation

HRID 2071143 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=2)[C:12]([O:14][CH3:15])=[O:13])[CH2:3]1.[NH4+].[Cl-].C[OH:24]>>[OH:1][C:2]1([OH:24])[CH2:6][CH2:5][N:4]([C:7]2[CH:16]=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=[C:9]([CH:8]=2)[C:17]([O:19][CH3:20])=[O:18])[CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 59569815HCID 59569815, compound

Product 1

HCID 59570148HCID 59570148, compoundYield 63%

Conditions

Temperature
80 °C

Procedure

Dimethyl 5-(3-oxopyrrolidin-1-yl)isophthalate (0.1114 g, 0.401 mmol, 1 eq) and NH4Cl (0.086 g, 1.61 mmol, 4 eq) in 5 ml anhydrous MeOH were heated to reflux at 80° C. for 22 h. After cooling to room temperature the solvent was removed in vacuo. The residue was stirred in EtOH and filtered through cotton to remove any insoluble material. Purification via flash chromatography yielded 0.082 g, (0.25 mmol, 63% yield) of dimethyl 5-(3,3-dihydroxypyrrolidin-1-yl)isophthalate.

Workup

  1. temperatureAfter cooling to room temperature the solvent
  2. customwas removed in vacuo
  3. filtrationfiltered through cotton
  4. customto remove any insoluble material
  5. customPurification via flash chromatography

Sources & evidence

ORD record
ord-dad7748fc685496aa2925beab6390879
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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