Methyl morpholine oxide → 1-Boc-piperidine-3-carboxaldehyde

HRID 970399Notes

Reaction equation

HRID 970399 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH2:14][OH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1>C(Cl)Cl.[Ru](=O)([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][CH:10]([CH:14]=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 99644481-Boc-piperidine-3-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 178457200HCID 178457200, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of N-(t-butoxycarbonyl)-3-hydroxymethylpiperidine (3741 mg, 17.4 mmol, Aldrich) in dry CH2Cl2 (250 mL) was added 4 angstrom molecular sieves (500 mg) and N-methyl-morpholine oxide (3054 mg, 26.1 mmol, Aldrich). After 10 min, tetrapropylammonium perruthenate oxide (305 mg, 0.87 mmol, Aldrich) and the reaction was stirred for 2 h. The reaction was filtered through a pad of silica gel and the silica gel was washed with EtOAc. The organic layers were and conc. in vacuo to a colorless oil which was used without further purification. MS (ESI) 214 (M+H).

Workup

  1. filtrationThe reaction was filtered through a pad of silica gel
  2. washthe silica gel was washed with EtOAc
  3. customwas used without further purification

Sources & evidence

ORD record
ord-5ef3f5e148d0405980f46bd91055e558
Source dataset
uspto-grants-2007_12
Patent number
US07312222B2

Reaction notes

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