Methyl morpholine oxide → HCID 68728543, compound

HRID 1182881Notes

Reaction equation

HRID 1182881 reaction equation
[OH:1][C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[CH:4]([C:5](=[O:22])[CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[OH:21])[C@H:3]1[CH2:23][CH3:24].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH2:23]([C@H:3]1[C:2](=[O:1])[CH2:19][CH2:18][C@@:17]2([CH3:20])[CH:4]1[C:5](=[O:22])[CH2:6][C@@H:7]1[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]1[CH2:9][CH2:10][C:11]2=[O:21])[CH3:24]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 68732249HCID 68732249, compound

Product 1

HCID 68728543HCID 68728543, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3α,17β-dihydroxy-4β-ethylandrostan-6-one and 3β-17β-dihydroxy-4β-ethylandrostan-6-one (179 mg) in DCM (6.7 ml) under N2, NMO (190 mg), TPAP (9.5 mg) and 4 Å molecular sieves (270 mg) were added. The mixture was stirred for 15 min and then SiO2 was added. The mixture was purified by flash chromatography (SiO2, n-hexane/EtOAc 70/30) to give the title compound (140 mg, 79%).

Workup

  1. additionSiO2 was added
  2. customThe mixture was purified by flash chromatography (SiO2, n-hexane/EtOAc 70/30)

Sources & evidence

ORD record
ord-9ae2a53267004148b5ab977cc8441297
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

Loading…