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

HRID 899714Notes

Reaction equation

HRID 899714 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[O:14])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateYield 89%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the above alcohol (0.79 g, 3.9 mmol) in CH2Cl2 (20 mL) was treated with molecular seives (1.95 g), N-methylmorpholine oxide (0.69 g, 5.9 mmol), and TPAP (0.14 g, 0.40 mmol). The mixture was stirred for 2 hours at room temperature and then filtered through a plug of silica gel, eluting with Et2O. The filtrate was then concentrated under reduced pressure to afford the desired 4-oxopiperidine-1-carboxylic acid tert-butyl ester (0.69 g, 89%). 1H NMR (CDCl3) δ 1.49 (s, 9H), 2.44 (t, 4H, J=7.0 Hz), 3.72 (t, 4H, J=7.0 Hz).

Workup

  1. filtrationfiltered through a plug of silica gel
  2. washeluting with Et2O
  3. concentrationThe filtrate was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-006774b419d1405ca1a0005b033f1efd
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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