Methyl morpholine oxide → HCID 86620751, compound

HRID 554317Notes

Reaction equation

HRID 554317 reaction equation
[Cl:1][C:2]1[C:3]([C:23](OCC)=[O:24])=[C:4]([CH3:22])[N:5]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].C([Al+]CC(C)C)C(C)C.C[N+]1([O-])CCOCC1>C1(C)C=CC=CC=1.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Cl:1][C:2]1[C:3]([CH:23]=[O:24])=[C:4]([CH3:22])[N:5]([S:13]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)(=[O:15])=[O:14])[C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 82029Methyl morpholine oxideHCID 21225700DiisobutylaluminumhydrideHCID 66924673HCID 66924673, compound

Product 1

HCID 86620751HCID 86620751, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 1140TolueneSolvent

Procedure

Using ethyl 4-chloro-2-methyl-5-phenyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate (610 mg), a 1.5 mol/L solution (6.0 mL) of diisobutylaluminum hydride in toluene, tetra-n-propylammonium perruthenate (53 mg), N-methylmorpholine N-oxide (195 mg) and molecular sieves 4A powder (300 mg), a procedure as in Reference Example 49 was performed to give the title compound as a pale-yellow solid (yield 301 mg, 55%).

Sources & evidence

ORD record
ord-0637536c21a6454bba084d545b872b2d
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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