Methyl morpholine oxide → HCID 56994186, compound

HRID 1859482Notes

Reaction equation

HRID 1859482 reaction equation
[C:1]([O:9][C@H:10]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@@H:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:24]([CH3:32])([CH2:25][CH2:26][C:27]=32)[C@@H:19]([C@H:20]([CH3:23])[CH2:21][OH:22])[CH2:18][CH:17]=4)[C:11]1([CH3:34])[CH3:33])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>CC(C)=O>[C:1]([O:9][C@H:10]1[CH2:30][CH2:29][C@@:28]2([CH3:31])[C@@H:12]([CH2:13][CH2:14][C:15]3[C:16]4[C@:24]([CH3:32])([CH2:25][CH2:26][C:27]=32)[C@@H:19]([C@@H:20]([CH:21]=[O:22])[CH3:23])[CH2:18][CH:17]=4)[C:11]1([CH3:33])[CH3:34])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 69997935HCID 69997935, compound

Product 1

HCID 56994186HCID 56994186, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

—Tetrapropylammonium perruthenate (0.180 g) was added to a solution of (3β,5α,20S)-4,4,20-trimethylpregna-8,14-diene-3,21-diol 3-benzoate (WO09852965; 4.62 g) and 4-methylmorpholine N-oxide (3.50 g) in acetone (80 ml). After 30 min. stirring at room temperature the reaction mixture was filtered over dicalite and silica. The filtrate was concentrated under reduced pressure, to give (3β,5α,20S)-3-(benzoyloxy)-4,4-dimethylpregna-8,14-diene-20-carboxaldehyde (4.28 g) which was used in the following step without further purification.

Workup

  1. filtrationwas filtered over dicalite and silica
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0d377df37ecf4e0e935452b1c71e48e9
Source dataset
uspto-grants-2003_03
Patent number
US06528501B1

Reaction notes

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