Triacetoxyperiodinane → Benzyl 4-formylpiperidine-1-carboxylate

HRID 220830Notes

Reaction equation

HRID 220830 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH2:39][OH:40])[CH2:35][CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl.C(Cl)(Cl)Cl.O>[CH2:23]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH:39]=[O:40])[CH2:35][CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 2776272Benzyl 4-formylpiperidine-1-carboxylateYield 66%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Dess-Martin reagent (17 g, 39.6 mmol) was added portion-wise to a solution of 4-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester from Example E33.1 (8.33 g, 33 mmol) in dichloromethane (100 ml) at room temperature. The mixture was stirred for 3 h under an inert atmosphere then diluted with chloroform and water and the layers were partitioned. The organic layer was washed with brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 40% EtOAc:60% hexane) to yield the title compound (5.5 g, 66%).

Workup

  1. customthe layers were partitioned
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (eluant; 40% EtOAc:60% hexane)

Sources & evidence

ORD record
ord-ce0d9e545c534132b12a3dca31da0c12
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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