Methyl morpholine oxide → HCID 22875685, compound

HRID 362801Notes

Reaction equation

HRID 362801 reaction equation
[OH:1][CH:2]([C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([NH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][C@@H:9]3[CH3:24])[CH2:6][CH2:5]1)[CH3:3].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:24][C@H:9]1[CH2:10][C@@H:11]2[C@:16]([CH3:17])([CH2:15][CH2:14][C:13](=[O:23])[NH:12]2)[C@@H:18]2[C@@H:8]1[C@H:7]1[C@:21]([CH3:22])([CH2:20][CH2:19]2)[C@@H:4]([C:2](=[O:1])[CH3:3])[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 22875678HCID 22875678, compound2×

Product 1

HCID 22875685HCID 22875685, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 20-hydroxy-7β-methyl-5α-4-azapregnan-3-one (22.3 gms, 67 mmol, product of Step 10) in dry methylene chloride under nitrogen (110 mL) was added 4-methyl morpholine N-oxide (11.8 gms, 100 mmol) followed by 4 Å molecular sieves (33 gm). To this mixture was added tetrapropylammonium perruthenate (1.2 gm). After stirring at room temperature for 4 h, the reaction mixture was poured through pad of silica gel in a 300 mL sintered glass funnel which was subsequently eluted with 4:1 ethyl acetate/methylene chloride (5 L). The solvent was removed by rotoevaporation and the title compound recrystallized.

Workup

  1. additionthe reaction mixture was poured through pad of silica gel in a 300 mL sintered glass funnel which
  2. washwas subsequently eluted with 4:1 ethyl acetate/methylene chloride (5 L)
  3. customThe solvent was removed by rotoevaporation
  4. customthe title compound recrystallized

Sources & evidence

ORD record
ord-32042e3fd0384302addec26abafb0d89
Source dataset
uspto-grants-1999_02
Patent number
US05872126

Reaction notes

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