N-Methylmorpholine N-oxide monohydrate → HCID 23369552, compound

HRID 1900803Notes

Reaction equation

HRID 1900803 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([CH:16]=[CH2:17])[O:13][C:5]2=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH:8]=[CH:7]2.[OH2:18].C[N+]1([O-])CC[O:23]CC1>C(O)(C)(C)C.CC(C)=O.O.[Os](=O)(=O)(=O)=O>[OH:18][CH:16]([CH:14]1[O:13][C:5]2=[C:6]3[C:11](=[C:2]([CH3:1])[CH:3]=[C:4]2[CH2:15]1)[NH:10][C:9](=[O:12])[CH:8]=[CH:7]3)[CH2:17][OH:23]

Participants

7

Reactant 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 23369618HCID 23369618, compound

Product 1

HCID 23369552HCID 23369552, compoundYield 152.7%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 6386tert-ButanolSolvent2×

Procedure

5-Methyl-2-vinyl-2,3,6,7-tetrahydrofuro-[2,3-f]-quinoline-7-one (1.5 g, 6.61 mmol) was dissolved in a solvent mixture of t-butanol (200 ml), acetone (200 ml) and water (100 ml). A solution (14 ml) of 0.16 N osmium tetraoxide and t-butanol, and N-methyl morpholine N-oxide hydrate (3.57 g, 3.46 mmol) were added to the mixture, and stirred at room temperature for 10 hours. The reaction mixture was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent=chloroform: methanol m 4:1) to obtain crude crystals. The obtained crude crystals were recrystallized from chloroform--methanol--ether to obtain 1.38 g of the title compound as colorless powdery crystals (80.0%).

Workup

  1. customcondensed under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (eluent=chloroform: methanol m 4:1)
  3. customto obtain crude crystals
  4. customThe obtained crude crystals
  5. customwere recrystallized from chloroform

Sources & evidence

ORD record
ord-67fafe4ee90d4efca660b9296576ebc6
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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