Methyl morpholine oxide → HCID 117727886, compound

HRID 61146Notes

Reaction equation

HRID 61146 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])[CH:4]([C:16]([O:18][CH3:19])=[O:17])[CH2:3]1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])[CH:4]([C:16]([O:18][CH3:19])=[O:17])[CH2:3]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 92019849Methyl 4-hydroxy-1-((S)-1-phenylethyl)piperidine-2-carboxylate

Product 1

HCID 117727886HCID 117727886, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl 4-hydroxy-1-((S)-1-phenylethyl)piperidine-2-carboxylate (3.4 g, 12.9 mmol), N-methylmorpholine N-oxide (3.0 g, 25.82 mmol) and 4 Å molecular sieves were stirred together in 15 mL of DCM at rt under argon. Tetra-n-propylammonium perruthenate (454 mg, 1.29 mmol) was then added slowly and reaction stirred for 5 h. The reaction was then filtered through silica and washed with 10% methanol in DCM and concentrated to give the title compound as a clear oil (3.34 g, 99%). MS (ESI) 262 (M+H).

Workup

  1. customreaction
  2. filtrationThe reaction was then filtered through silica
  3. washwashed with 10% methanol in DCM
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b3b97f384e284ea88de3f8fbfe00a870
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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