N-Methylmorpholine N-oxide monohydrate → 2808-12-0

HRID 420766Notes

Reaction equation

HRID 420766 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C@H:5]1[CH2:10][CH2:9][CH2:8][C@@H:7]([OH:11])[CH2:6]1.O.C[N+]1([O-])CCOCC1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH2:6]1

Participants

5

Reactant 2

HCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 57577344Rac-cis (3-hydroxy-cyclohexyl)-acetic acid methyl ester

Product 1

HCID 5660952808-12-0

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

rac-cis-(3-Hydroxy-cyclohexyl)-acetic acid methyl ester (500 mg, 2.90 mmol) (Example 5, step 1) was dissolved in 2 ml dichloromethane and tetrapropylammonium perruthenate [TPAP] (102 mg, 0.29 mmol) and 4-methylmorpholine oxide monohydrate (590 mg, 4.35 mmol) were added. The reaction mixture was stirred for 16 hours at room temperature, filtered over dicalite and evaporated to dryness. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0→50:50 gradient). The desired compound was obtained as a light yellow liquid (240 mg, 48%).

Workup

  1. filtrationfiltered over dicalite
  2. customevaporated to dryness
  3. customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0→50:50 gradient)

Sources & evidence

ORD record
ord-cb0e570cbeaf4cb9b95e377c6d650161
Source dataset
uspto-grants-2012_01
Patent number
US08097637B2

Reaction notes

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