Methyl morpholine oxide → HCID 22874155, compound

HRID 1684566Notes

Reaction equation

HRID 1684566 reaction equation
[F:1][C:2]([F:30])([F:29])[CH2:3][CH2:4][CH2:5][CH:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:9]12[CH3:10])[C@:22]1([CH3:23])[C:17]([CH:18]=[C:19]([CH2:27][OH:28])[CH2:20][CH2:21]1)=[CH:16][CH2:15]3)[OH:7].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:1][C:2]([F:29])([F:30])[CH2:3][CH2:4][CH2:5][C:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:9]12[CH3:10])[C@:22]1([CH3:23])[C:17]([CH:18]=[C:19]([CH:27]=[O:28])[CH2:20][CH2:21]1)=[CH:16][CH2:15]3)=[O:7]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 53978241HCID 53978241, compound

Product 1

HCID 22874155HCID 22874155, compound

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Tetrapropyl ammonium perruthenate (10 mg, 0.028 mmol) was added to a solution of (17β)-17-(5,5,5-trifluoro-1-hydroxypentyl)-androsta-3,5-diene-3-methanol (65 mg, 0.15 mmol) and 4-methylmorpholine N-oxide (80 mg, 0.68 mmol) in CH2Cl2 (2.0 ml) at RT. After 1 h the reaction was flash chromatographed (silica gel, 20% EtOAc/80% hexanes) to yield the title compound.

Workup

  1. customflash chromatographed (silica gel, 20% EtOAc/80% hexanes)

Sources & evidence

ORD record
ord-7d5283e5392447f3a02f515c617c22b7
Source dataset
uspto-grants-1997_06
Patent number
US05641765

Reaction notes

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