Methyl morpholine oxide → HCID 86669943, compound

HRID 1506565Notes

Reaction equation

HRID 1506565 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH2:17][CH2:16][C:15]4[CH:19]=[C:20]([CH:23]=C)[CH:21]=[CH:22][C:14]=4[C:13]=3[CH:12]=[N:11]2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].C[N+]1([O-])CC[O:29]CC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.[Os](=O)(=O)(=O)=O.O>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[CH2:17][CH2:16][C:15]4[CH:19]=[C:20]([CH:23]=[O:29])[CH:21]=[CH:22][C:14]=4[C:13]=3[CH:12]=[N:11]2)=[CH:6][CH:5]=1)[CH2:2][CH3:3]

Participants

8

Reactant 3

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 67169434HCID 67169434, compound

Product 1

HCID 86669943HCID 86669943, compound

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 30318Osmium TetroxideSolvent

Procedure

To a clear solution of 3-(4-propylphenyl)-7-vinyl-4,5-dihydro-3H-benzo[e]indazole (Preparation 136E, 85 mg, 0.270 mmol) in THF (5 mL) were sequentially added NMO in water (0.090 mL, 0.433 mmol) and osmium tetroxide in water (0.066 mL, 10.81 μmol) at room temperature. The solution was vigorously stirred at room temperature overnight. Sodium periodate (116 mg, 0.541 mmol) in water (2 mL) was added. The mixture was stirred at room temperature under nitrogen for 2 hours. A white solid precipitated out. Water (2 mL) was then added and the solid was filtered, washed with water (2×2 mL) and dried to give 65 mg crude product which was used directly for the next step. LC/MS M+1=317.1. The product had an HPLC retention time=3.92 min. (condition A);

Workup

  1. customat room temperature
  2. stirringThe mixture was stirred at room temperature under nitrogen for 2 hours
  3. customA white solid precipitated out
  4. additionWater (2 mL) was then added
  5. filtrationthe solid was filtered
  6. washwashed with water (2×2 mL)
  7. customdried

Sources & evidence

ORD record
ord-7ed9bb740662489fa1842949cd493000
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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