Methyl morpholine oxide → Tert-butyl 2-(3-oxopropyl)piperidine-1-carboxylate

HRID 899600Notes

Reaction equation

HRID 899600 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][CH2:16][OH:17])=[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][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][CH:16]=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 10900840Tert-butyl 2-(3-hydroxypropyl)piperidine-1-carboxylate

Product 1

HCID 11096761Tert-butyl 2-(3-oxopropyl)piperidine-1-carboxylateYield 86.7%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-tert-butoxycarbonyl-3-piperidin-2-yl-propan-1-ol (0.372 g, 1.53 mmol) in CH2Cl2 (7.5 mL), at room temperature, was added sequentially 3Å molecular sieves (0.814 g), N-methylmorpholine N-oxide (0.278 g, 2.37 mmol) and tetrapropylammonium perruthenate (56 mg, 0.16 mmol). After 90 minutes, the mixture was filtered through a short column of silica gel and the cake was washed with ethyl acetate. The solvent was removed from the filtrate under reduced pressure to provide 0.32 g (86%) of N-tert-butoxycarbonyl-3-piperidin-2-yl-propionaldehyde as a green oil which was used without further purification.

Workup

  1. filtrationthe mixture was filtered through a short column of silica gel
  2. washthe cake was washed with ethyl acetate
  3. customThe solvent was removed from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-78f82001069347779c10709bd765cac9
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

Loading…