Hydrogen Peroxide → 1-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-hydroxypropyl)-2-oxopyrrolidine

HRID 323497Notes

Reaction equation

HRID 323497 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH2:12][CH:13]=[CH2:14])[C:8]1=[O:23].C12BC(CCC1)CCC2.[OH-:40].[Na+].OO>O1CCCC1.CO.ClCCl>[CH3:30][O:29][C:25]1[CH:24]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:26]=1[O:27][CH3:28])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH2:12][CH2:13][CH2:14][OH:40])[C:8]1=[O:23]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 220093331-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(allyl)-2-oxopyrrolidine

Product 1

HCID 184644801-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-hydroxypropyl)-2-oxopyrrolidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

Combine 1-(3,4,5-trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(allyl)-2-oxopyrrolidine (0.677 g, 1.64 mmol) and tetrahydrofuran (10 mL). Add dropwise a solution of 9-BBN (9-borabicyclo[3.3.1]nonane) (5.56 mL, 0.5 M, 2.78 mmol) in tetrahydrofuran. After 1.5 hours, add dropwise an aqueous sodium hydroxide solution (10 mL, 1 M) and 30% aqueous hydrogen peroxide (1.5 mL, about 14.7 mmol). After 15 minutes heat the reaction mixture to reflux. After 1 hour, cool to ambient temperature, saturate the aqueous mixture with potassium carbonate and separate the layers. Extract the aqueous layer five times with diethyl ether. Combine the organic layers and dry over potassium carbonate, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% methanol/dichloromethane to give the title compound.

Workup

  1. temperatureAfter 15 minutes heat the reaction mixture
  2. temperatureto reflux
  3. waitAfter 1 hour
  4. concentrationsaturate the aqueous mixture with potassium carbonate
  5. customseparate the layers
  6. extractionExtract the aqueous layer five times with diethyl ether
  7. dry with materialdry over potassium carbonate
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue

Sources & evidence

ORD record
ord-e0fe1c64531a4978b2bce8b2f5d10326
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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