Water → HCID 58415410, compound

HRID 46178Notes

Reaction equation

HRID 46178 reaction equation
[CH2:1]([C:4]1([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2=[N:13][CH:14]=[CH:15][N:5]12)[CH:2]=[CH2:3].[OH2:23].C[N+]1([O-])CC[O:28]CC1>CC(C)=O.O=[Os](=O)(=O)=O>[Br:22][C:19]1[CH:18]=[CH:17][C:16]([C:4]2([CH2:1][CH:2]([OH:28])[CH2:3][OH:23])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]3=[N:13][CH:14]=[CH:15][N:5]23)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxide2×HCID 462056095-allyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole

Product 1

HCID 58415410HCID 58415410, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalyst3×HCID 180AcetoneSolvent

Procedure

To a solution of 5-allyl-5-(4-bromophenyl)-5H-imidazo[2,1-a]isoindole (150 mg) in acetone (5.5 mL) was added water (1 mL) followed by NMO (60 mg) and OsO4 (0.536 mL, 2.5% in tert-BuOH). After stirring at room temperature for 24 h, 100 mg NMO and 0.1 mL OsO4 solution were added. After 9 h 0.1 mL more OsO4 solution was added and stirred at room temperature over the weekend. The reaction was then quenched with 1:1 aqueous saturated NaHCO3:Na2SO3 and partitioned between aqueous saturated NaHCO3 and EtOAc. Aqueous layer was extracted with EtOAc (3×). Combined organic layers were dried over Na2SO4 and concentrated. Purification by reversed phase HPLC (21×100 mm Phenomenex Gemini, 5-40% MeCN/water containing 0.1% TFA over 20 min at 20 mL/min) to give title compound as a white solid. Mass. found (M+H)+, 387.0.

Workup

  1. stirringstirred at room temperature over the weekend
  2. customThe reaction was then quenched with 1:1 aqueous saturated NaHCO3
  3. customNa2SO3 and partitioned between aqueous saturated NaHCO3 and EtOAc
  4. extractionAqueous layer was extracted with EtOAc (3×)
  5. dry with materialCombined organic layers were dried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by reversed phase HPLC (21×100 mm Phenomenex Gemini, 5-40% MeCN/water containing 0.1% TFA over 20 min at 20 mL/min)

Sources & evidence

ORD record
ord-a398d753743c44eeb7ff93305f29071e
Source dataset
uspto-grants-2013_09
Patent number
US08541595B2

Reaction notes

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