Methyl morpholine oxide → tert-Butyl 4-formylpiperidine-1-carboxylate

HRID 1179345Notes

Reaction equation

HRID 1179345 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateYield 65.5%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of the product of Example 1 (23.1 g), 4-methylmorpholine N-oxide (NMO, 18.9 g) and 4A molecular sieves (53.5 g) in DCM (214 mL) was added tetrapropylammonium perruthenate (TPAP, 1.9 g) portion-wise at room temperature. The reaction mixture was stirred at room temperature for 1 h and filtered through a pad of silica gel. Evaporation of solvent gave the title compound as a light yellow oil (15.0 g).

Workup

  1. filtrationfiltered through a pad of silica gel
  2. customEvaporation of solvent

Sources & evidence

ORD record
ord-91ac4130c9dd42b38103f825b1facde9
Source dataset
uspto-grants-2007_10
Patent number
US07279491B2

Reaction notes

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