Methanol → HCID 58218785, compound

HRID 1020972Notes

Reaction equation

HRID 1020972 reaction equation
[OH:1][CH:2](CO)[CH2:3][C:4]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:8][C:7](=[O:9])[N:6]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])[CH2:5]1.O.CO>C1COCC1.C(OCC)(=O)C>[CH3:16][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:17])[C:10]=1[N:6]1[C:7](=[O:9])[CH2:8][C:4]([CH2:3][CH:2]=[O:1])([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:5]1

Participants

6

Reactant 3

HCID 887MethanolHCID 962WaterHCID 58218765HCID 58218765, compound

Product 1

HCID 58218785HCID 58218785, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 3-(2,3-dihydroxypropyl)-1-(2,6-dimethylphenyl)-5-oxopyrrolidine-3-carboxylate (1.2 g, 3.3 mmol) dissolved in THF (8 mL) was treated with NaIO4 (1.4 g, 6.6 mmol) and water (2 mL). After stirring overnight at room temperature, methanol (2 mL) was added and the mixture was diluted with ethyl acetate (15 mL) and washed with water. The aqueous phase was washed with ethyl acetate and the organic layers were combined, dried and the solvent evaporated. The residue was purified by flash chromatography (SiO2, 10-100% EtOAc/hexanes) to yield tert-butyl 1-(2,6-dimethylphenyl)-5-oxo-3-(2-oxoethyl)pyrrolidine-3-carboxylate (980 mg, 88% yield). LC-MS Rt (retention time): 2.28 min, MS: (ES) m/z 332 (M+H+).

Workup

  1. washwashed with water
  2. washThe aqueous phase was washed with ethyl acetate
  3. customdried
  4. customthe solvent evaporated
  5. customThe residue was purified by flash chromatography (SiO2, 10-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2dbc0db4d3134e398eb6d023c91ebd35
Source dataset
uspto-grants-2014_05
Patent number
US08716494B2

Reaction notes

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