Methyl morpholine oxide → HCID 88314422, compound

HRID 1847116Notes

Reaction equation

HRID 1847116 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH:5]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[CH:7]([C:8](=[O:33])[O:9][C:10]3[C@H:11]4[C@:24]([CH3:32])([CH2:25][CH2:26][C:27]=32)[C@@H:14]([C@H:15]([CH3:23])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:22])[CH2:20][OH:21])[CH2:13][CH2:12]4)[CH2:6]1.C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.ClCCl>[CH3:1][O:2][CH2:3][O:4][CH:5]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[CH:7]([C:8](=[O:33])[O:9][C:10]3[C@H:11]4[C@:24]([CH3:32])([CH2:25][CH2:26][C:27]=32)[C@@H:14]([C@H:15]([CH3:23])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:22])[CH:20]=[O:21])[CH2:13][CH2:12]4)[CH2:6]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67609814HCID 67609814, compound

Product 1

HCID 88314422HCID 88314422, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (2 mL) containing compound 62 (10.8 mg, 0.0234 mmol) obtained in Example 52, Molecular Sieves 4 Å (200 mg), 4-methylmorpholin-N-oxide (10 mg, 0.085 mmol) and tetrapropylammonium perruthenate (3.0 mg, 0.0085 mmol) were added, followed by stirring at room temperature for 15 minutes. The reaction mixture was filtered, and the filtrate was concentrated, followed by purification by silica gel column chromatography (20 to 50% ethyl acetate/n-hexane) to obtain the title compound (4.5 mg, 42%).

Workup

  1. additionwere added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customfollowed by purification by silica gel column chromatography (20 to 50% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-3f60c739da8f4861a1675b6fff099b49
Source dataset
uspto-grants-2015_02
Patent number
US08952003B2

Reaction notes

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