Methyl morpholine oxide → HCID 68730500, compound

HRID 1182890Notes

Reaction equation

HRID 1182890 reaction equation
[C:1]([O:4][C@@H:5]1[CH:22]([OH:23])[CH2:21][CH2:20][C@@:19]2([CH3:24])[CH:6]1[CH2:7][CH2:8][C@@H:9]1[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]1[CH2:11][CH2:12][C@@H:13]2[OH:25])(=[O:3])[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[C:1]([O:4][C@@H:5]1[C:22](=[O:23])[CH2:21][CH2:20][C@@:19]2([CH3:24])[CH:6]1[CH2:7][CH2:8][C@@H:9]1[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]1[CH2:11][CH2:12][C:13]2=[O:25])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 68729036HCID 68729036, compound

Product 1

HCID 68730500HCID 68730500, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the 3α:3β mixture of 4α-acetoxyandrostan-3,17β-diol (380 mg), TPAP (38 mg), NMO (383 mg) under N2 in DCM (15 ml) was stirred in the presence of 4 Å molecular sieves (540 mg) for 1 h. The mixture was filtered and the filtrate was purified by flash chromatography (SiO2, n-hexane/EtOAc 7/3) to give the title compound (353 mg, 93%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was purified by flash chromatography (SiO2, n-hexane/EtOAc 7/3)

Sources & evidence

ORD record
ord-cbc69a38afa643ada4cbd91a8b504c8e
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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