Hydrogen Peroxide → HCID 68899835, compound

HRID 1394932Notes

Reaction equation

HRID 1394932 reaction equation
[CH3:1][C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH2:4][N:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[OH2:20].[OH-].[Na+].OO>C1COCC1>[OH:20][CH:5]1[CH2:4][N:3]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C:2]([CH3:1])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 68896125HCID 68896125, compound

Product 1

HCID 68899835HCID 68899835, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 20-4 (0.50 g, 1.9 mmol) in anhydrous THF (80 mL) at 0° C. was treated with BH3:THF (1.93 mL, 1.9 mmol) then stirred for 1 hour. at 25° C. Water (0.35 mL, 19.2 mmol) was added, followed by 3 N NaOH (0.23 mL, 5.8 mmol). The resulting solution was cooled to 0° C. prior to the addition of 30% H2O2 (0.22 mL, 1.9 mmol). The reaction was partitioned between sat. aq. NaHCO3 (100 mL) and EtOAc (2×100 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column (SiO2, O-100% EtOAc/Hexanes gradient) to yield tert-butyl 4-hydroxy-2-methyl-2-phenylpyrrolidine-1-carboxylate, 20-5: LRMS m/z (M+H) 278.2 found, 278.1 required.

Workup

  1. customat 25° C
  2. customThe reaction was partitioned between sat. aq. NaHCO3 (100 mL) and EtOAc (2×100 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column (SiO2

Sources & evidence

ORD record
ord-a2b4a5b95f77496da64dd479993e1ffb
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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