Methyl morpholine oxide → HCID 15429326, compound

HRID 1831736Notes

Reaction equation

HRID 1831736 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:7]3[CH2:16][CH2:15][CH2:14][CH:8]3[C:9](=[O:13])[NH:10][C:11]=2[CH:12]=1.C[N+]1([O-])CCOCC1>C(Cl)(Cl)Cl.ClCCl.C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH2:16]1[CH:7]2[CH:8]([C:9](=[O:13])[NH:10][C:11]3[CH:12]=[C:3]([CH:2]=[O:1])[CH:4]=[CH:5][C:6]=32)[CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 15429325HCID 15429325, compound

Product 1

HCID 15429326HCID 15429326, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalyst2×HCID 87937131HCID 87937131, compoundSolvent

Procedure

A solution of 187 mg (0.86 mmol) of 7-hydroxymethyl-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one in 20 ml of chloroform-dichloromethane-acetonitrile (2:1:1) is mixed with 151 mg (1.29 mmol) of N-methylmorpholin-N-oxide and 1.5 g of molecular sieve 4 Å. After 15 mg (0.043 mmol) of tetrapropylammonium perruthenate (TPAP) is added, the batch is stirred for 2.5 hours at room temperature, before another 10 mg (0.028 mmol) of TPAP is added. After 1.5 hours, silica gel is added to the reaction mixture, and the solvent is distilled off in a vacuum. Column chromatography with hexane-ethyl acetate yields 156 mg of product.

Workup

  1. additionis added
  2. additionsilica gel is added to the reaction mixture
  3. distillationthe solvent is distilled off in a vacuum

Sources & evidence

ORD record
ord-ff66b1c7ea154e2f832e02b12dcbc224
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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