Methyl morpholine oxide → Benzyl (R)-2-methyl-5-oxopiperidine-1-carboxylate

HRID 81145Notes

Reaction equation

HRID 81145 reaction equation
[OH:1][C@@H:2]1[CH2:7][N:6]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[C@H:5]([CH3:18])[CH2:4][CH2:3]1.C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH3:18][C@@H:5]1[CH2:4][CH2:3][C:2](=[O:1])[CH2:7][N:6]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 866818641-Piperidinecarboxylic acid, 5-hydroxy-2-methyl-, phenylmethyl ester, (2R,5S)-

Product 1

HCID 86724499Benzyl (R)-2-methyl-5-oxopiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzyl (2R,5S)-5-hydroxy-2-methylpiperidine-1-carboxylate (6.8 g, 27.3 mmol) was dissolved in DCM (100 mL) containing crushed molecular sieves. N-methylmorpholine N-oxide (4.15 g, 35.5 mmol) and tetrapropylammonium perruthenate (0.48 g, 1.36 mmol) were added, and the reaction was stirred at room temperature for 1.5 hours. The mixture was filtered through a celite pad and concentrated. The residue was purified by silica gel chromatography (0-30% ethyl acetate/hexanes, linear gradient) to afford benzyl (2R)-2-methyl-5-oxopiperidine-1-carboxylate. MS ESI calc'd. for C14H17NO3 [M+H]+ 248. found 248.

Workup

  1. additioncontaining
  2. customcrushed molecular sieves
  3. filtrationThe mixture was filtered through a celite pad
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0-30% ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record
ord-5d63f5bb08fc4769bfc8486fa601c8de
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

Loading…