Methyl morpholine oxide → HCID 23249714, compound

HRID 1274486Notes

Reaction equation

HRID 1274486 reaction equation
[CH3:1][C:2]1([CH3:15])[O:7][CH:6]([C:8]([CH3:14])([CH:10]([OH:13])[CH2:11][CH3:12])[CH3:9])[CH2:5][CH2:4][O:3]1.C[N+]1([O-])CCOCC1>C(Cl)Cl>[CH3:15][C:2]1([CH3:1])[O:7][CH:6]([C:8]([CH3:14])([C:10](=[O:13])[CH2:11][CH3:12])[CH3:9])[CH2:5][CH2:4][O:3]1

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 22244497HCID 22244497, compound

Product 1

HCID 23249714HCID 23249714, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

70 mg (0.32 mmol) of alcohol 46 is dissolved in 5 ml of CH2Cl2, and 6 4A molecular sieve spheres and 66 mg (0.48 mmol, 1.5 equivalents) of 4-methylmorpholine N-oxide (NMO) are added. After 10 minutes of stirring, 6 mg of tetrapropylammonium-perruthenate(VII) (TPAP) (0.016 mmol, 0.05 equivalent) is added and stirred for 4 hours at room temperature. Then, the reaction mixture is concentrated by evaporation in a rotary evaporator and directly purified by column chromatography with pentane:ether=1:1. 60 mg (0.28 mmol) of ethyl ketone 2, corresponding to a yield of 86%, is obtained.

Workup

  1. stirringstirred for 4 hours at room temperature
  2. concentrationThen, the reaction mixture is concentrated by evaporation in a rotary evaporator
  3. customdirectly purified by column chromatography with pentane

Sources & evidence

ORD record
ord-00881bd548364d7abf4f2cc7b31ddfdd
Source dataset
uspto-grants-2000_12
Patent number
US06156905

Reaction notes

Loading…