Methyl morpholine oxide → HCID 86659816, compound

HRID 1846354Notes

Reaction equation

HRID 1846354 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1.C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[CH:13][N:14]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67455467HCID 67455467, compound

Product 1

HCID 86659816HCID 86659816, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

(6-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-3-yl)methanol (1.3 g, 6.0 mmol) was dissolved in CH2Cl2 (80 mL) and NMO (0.846 g, 7.2 mmol) and TPAP (0.210 g, 0.6 mmol) were added. After stirring at room temperature for 20 minutes, the reaction mixture was filtered through Celite®, and the filtrate was concentrated. Purification of the residue by flash chromatography on silica gel, eluting with 30% ethyl acetate/heptane to 75% ethyl acetate/heptane, afforded 6-((tetrahydro-2H-pyran-2-yloxy)methyl)nicotinaldehyde as a yellow oil (0.560 g, 42%).

Workup

  1. filtrationthe reaction mixture was filtered through Celite®
  2. concentrationthe filtrate was concentrated
  3. customPurification of the residue by flash chromatography on silica gel
  4. washeluting with 30% ethyl acetate/heptane to 75% ethyl acetate/heptane

Sources & evidence

ORD record
ord-64e55f13bee74537a239a7be9b270413
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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