Methyl morpholine oxide → HCID 18173035, compound

HRID 395870Notes

Reaction equation

HRID 395870 reaction equation
C=C1[CH:7]2[CH:5]3[CH:6]2CC1[CH:4]3[C:9]1[NH:17][C:16]2[C:15](=[O:18])[N:14]([CH2:19][CH2:20][CH3:21])[C:13](=[O:22])[N:12]([CH2:23][CH2:24][CH3:25])[C:11]=2[N:10]=1.C[N+]1([O-])CC[O:30][CH2:29]C1.[CH3:34][C:35]([CH3:37])=[O:36].O>O=[Os](=O)(=O)=O>[OH:36][C:35]1([CH2:29][OH:30])[CH:37]2[CH:5]3[CH:6]2[CH2:7][CH:34]1[CH:4]3[C:9]1[NH:17][C:16]2[C:15](=[O:18])[N:14]([CH2:19][CH2:20][CH3:21])[C:13](=[O:22])[N:12]([CH2:23][CH2:24][CH3:25])[C:11]=2[N:10]=1

Participants

5

Reactant 3

HCID 82029Methyl morpholine oxideHCID 18173107HCID 18173107, compoundHCID 18366337Propan-2-one--water (1/1)

Product 1

HCID 18173035HCID 18173035, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

8-(5-Methylene-tricyclo[2.2.1.02,6]hept-3-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (284 mg) was taken in acetone:water (1:1, 5 ml) at 0° C. OsO4 (2 ml) was added and the mixture was stirred for 15 min. N-Methylmorpholine-N-oxide (120 mg) was added and the mixture was stirred at room temperature overnight. The next day the reaction mixture was quenched with NaHSO3 solution, extracted with ethyl acetate (3×25 ml). Combined organic layer was washed with water, brine and dried over Na2SO4. After concentration the crude product was purified on a silica column. (ES+ 375)

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe next day the reaction mixture was quenched with NaHSO3 solution
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. washCombined organic layer was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentration the crude product
  7. customwas purified on a silica column

Sources & evidence

ORD record
ord-d336f5f982344e5384699fbc2fba7925
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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