Methyl morpholine oxide → HCID 59326830, compound

HRID 1880182Notes

Reaction equation

HRID 1880182 reaction equation
[F:1][C:2]1[C:7]([CH:8]2[CH2:13][CH2:12]S[CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.C[N+]1([O-])CCOCC1.[S:22]([O-:25])(O)=[O:23].[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O>[O:23]=[S:22]1(=[O:25])[CH2:10][CH2:9][CH:8]([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 67415993HCID 67415993, compound

Product 1

HCID 59326830HCID 59326830, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a stirred mixture of 2-fluoro-3-(tetrahydro-2H-thiopyran-4-yl)pyridine (1.2 g, 6.08 mmol), 4-methylmorpholine 4-oxide (1.781 g, 15.21 mmol) in acetone/water (7:3, 30 mL) was added osmium(VIII) oxide (0.631 mL, 0.304 mmol). Stirring was continued at RT overnight. A saturated solution of sodium hydrogensulfite (10 mL) was added and stirred in 15 min., extracted with EtOAc (3×), dried over MgSO4, concentrated to give the tan solid. MS (M+1): 230.2.

Workup

  1. stirringstirred in 15 min.
  2. extractionextracted with EtOAc (3×)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give the tan solid

Sources & evidence

ORD record
ord-f278d6ae811540fbb0df1dfb4702b593
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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