Methyl morpholine oxide → HCID 86620770, compound

HRID 554350Notes

Reaction equation

HRID 554350 reaction equation
[Br:1][C:2]1[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:5]=[C:4]([C:16](OC)=[O:17])[C:3]=1[CH:20]([CH3:22])[CH3:21].[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>[Br:1][C:2]1[N:6]([S:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:5]=[C:4]([CH:16]=[O:17])[C:3]=1[CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 82029Methyl morpholine oxideHCID 21225700DiisobutylaluminumhydrideHCID 66924920HCID 66924920, compound

Product 1

HCID 86620770HCID 86620770, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 1140TolueneSolvent

Procedure

Using methyl 5-bromo-4-isopropyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate (4.8 g), and a 1.5 mol/L solution (50 mL) of diisobutylaluminum hydride in toluene, tetra-n-propylammonium perruthenate (218 mg), N-methylmorpholine N-oxide (1.6 g) and molecular sieves 4A powder (2.5 g), a procedure as in Reference Example 6 was performed to give crude 5-bromo-4-isopropyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (3.83 g) as an oil. Furthermore, using 40% methylamine methanol solution (877 mg), sodium borohydride (474 mg) and crude 5-bromo-4-isopropyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (3.83 g), a procedure as in Reference Example 66 was performed to give the title compound as a colorless oil (yield 502 mg, 11%).

Sources & evidence

ORD record
ord-0e3b77b260d84f2497d9bba75cc1be57
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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