Dichloromethane → (2R)-6-oxohexane-1,2-diyl dinitrate

HRID 1361923Notes

Reaction equation

HRID 1361923 reaction equation
ClCCl.[N+:4]([O-:18])([O:6][CH2:7][C@H:8]([O:14][N+:15]([O-:17])=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[O:5].C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.O>[N+:4]([O-:18])([O:6][CH2:7][C@H:8]([O:14][N+:15]([O-:17])=[O:16])[CH2:9][CH2:10][CH2:11][CH:12]=[O:13])=[O:5]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 82029Methyl morpholine oxideHCID 59556786(2R)-6-hydroxyhexane-1,2-diyl dinitrate2×

Product 1

HCID 86622539(2R)-6-oxohexane-1,2-diyl dinitrate

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 962WaterSolvent

Procedure

Tetrapropylammonium perruthenate (16 mg, 0.05 mmol) was added to a dichloromethane (5 mL) solution of (2R)-6-hydroxyhexane-1,2-diyl dinitrate (intermediate 2, 105 mg, 0.49 mmol) and 4-methylmorpholine N-oxide (137 mg, 1.17 mmol). The solution was stirred at room temperature for 30 minutes. Water was added and the solution was extracted with dichloromethane. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography over silica eluting with ethyl acetate/hexanes afforded the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 9.79 (s, 1H), 5.25-5.32 (m, 1H), 4.76 (dd, J=13.0, 3.5 Hz, 1H), 4.49 (dd, J=13.0, 6.5 Hz, 1H), 2.59-2.54 (m, 2H), 1.83-1.73 (m, 4H).

Workup

  1. extractionthe solution was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e11987059e2043e0a297ba8fce27c009
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

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