Acetone → HCID 117849123, compound

HRID 1477638Notes

Reaction equation

HRID 1477638 reaction equation
CC(C)=[O:3].[CH3:5][O:6][C:7]1[N:12]=[C:11]([C:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=2)[CH:10]=[CH:9][CH:8]=1.C[N+]1([O-])CCOCC1.[OH2:34]>[Os](=O)(=O)(=O)=O>[OH:34][CH:18]1[C:13]([OH:3])([C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([O:6][CH3:5])[N:12]=2)[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17]1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 82029Methyl morpholine oxideHCID 117839633HCID 117839633, compound

Product 1

HCID 117849123HCID 117849123, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To an acetone (10 mL)-water (1.0 mL) solution of tert-butyl 6-methoxy-5′,6′-dihydro-[2,4′-bipyridine]-1′(2′H)-carboxylate (1.00 g, 3.44 mmol) synthesized in Reference Synthesis Example 184, supported osmium tetroxide (276 mg, 0.102 mmol, osmium content 9.4%, manufactured by Wako Pure Chemical Industries, Ltd.) and N-methylmorpholine-N-oxide (1.20 g, 10.3 mmol) were added and the resultant mixture was stirred at room temperature for 6 days. After completion of the reaction, the reaction solution was filtered and ethyl acetate was added to the filtrate, followed by washing the resultant mixture with saturated ammonium chloride aqueous solution and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain the title compound (1.01 g, yield 91%).

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. filtrationthe reaction solution was filtered
  4. additionethyl acetate was added to the filtrate
  5. washby washing the resultant mixture with saturated ammonium chloride aqueous solution and brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-530e7207ae3a485e8e9e1c0f4b642ce7
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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