Methyl morpholine oxide → HCID 86651518, compound

HRID 1912742Notes

Reaction equation

HRID 1912742 reaction equation
[CH:1]([O:3][C@@H:4]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[CH:6]([C@@H:7]([OH:24])[CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[OH:23])[CH2:5]1)=[O:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH:1]([O:3][C@@H:4]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[CH:6]([C:7](=[O:24])[CH2:8][C@@H:9]3[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]3[CH2:11][CH2:12][C:13]2=[O:23])[CH2:5]1)=[O:2]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 86651517HCID 86651517, compound

Product 1

HCID 86651518HCID 86651518, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3α-formyloxyandrostane-6α,17β-diol (2.50 g) in CH2Cl2 (100 mL), NMO (2.7 g) and molecular sieves (4 Å, 3.8 g) were added followed by the addition of TPAP (270 mg). After stirring for 2 h at room temperature, the solvent was removed and the mixture purified by flash chromatography (SiO2, n-hexane/EtOAc 65/35) to give 3α-formyloxyandrostane-6,17-dione in 90% yield as a white solid. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 8.15 (1H, s), 5.12 (1H, bs), 2.40-0.90 (20H, m), 0.77 (3H, s), 0.66 (3H, s).

Workup

  1. customthe solvent was removed
  2. customthe mixture purified by flash chromatography (SiO2, n-hexane/EtOAc 65/35)

Sources & evidence

ORD record
ord-dee07aa9520f479eadf807eccf8556bd
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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