Methyl morpholine oxide → 1-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-one

HRID 1907745Notes

Reaction equation

HRID 1907745 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[CH2:15][CH2:14][C:13]([OH:16])=[CH:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[CH2:15][CH2:14][C:13](=[O:16])[CH2:12]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 867621701-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolin-3-ol

Product 1

HCID 218216451-(Benzo[d][1,3]dioxol-5-ylmethyl)pyrrolidin-3-oneYield 84%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of alcohol 273 (0.78 g, 3.53 mmol) in dry DCM (40 mL) was treated with 4 Å molecular sieves (powder, 3.49 g) and 4-methylmorpholine N-oxide (NMO) (2.11 g, 18.03 mmol) and the suspension was stirred under nitrogen atmosphere for 18 h. The reaction mixture was cooled to 0° C. for the addition of solid tetrapropylammonium perruthenate (TPAP) (0.11 g, 0.31 mmol) and stirred for 30 min, then diluted with DCM, filtered through a Celite® pad, washed with saturated NaHCO3, dried over MgSO4, filtered through a pad of SiO2 (eluent: 5% MeOH in DCM) and concentrated to provide title compound 274 (0.65 g, 84% yield).

Workup

  1. stirringstirred for 30 min
  2. filtrationfiltered through a Celite® pad
  3. washwashed with saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through a pad of SiO2 (eluent: 5% MeOH in DCM)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9b36b7a08e2b4abab064feb952cc57ba
Source dataset
uspto-grants-2013_12
Patent number
US08598168B2

Reaction notes

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