1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide → HCID 86670627, compound

HRID 407195Notes

Reaction equation

HRID 407195 reaction equation
[C:1]([C:3]1([C:16]2[CH:21]=[C:20]([CH2:22][OH:23])[CH:19]=[CH:18][N:17]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2].OI1(=O)C2C=CC=CC=2C(=O)O1>C(#N)C>[C:1]([C:3]1([C:16]2[CH:21]=[C:20]([CH:22]=[O:23])[CH:19]=[CH:18][N:17]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#[N:2]

Participants

4

Reactant 2

HCID 3394961-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxideHCID 67153735HCID 67153735, compound

Product 1

HCID 86670627HCID 86670627, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl 4-cyano-4-[4-(hydroxymethyl)pyridine-2-yl]piperidine-1-carboxylate (see Example 23, 0.465 g, 1.46 mmol) in 7 mL of acetonitrile was added 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide (1.23 g, 4.39 mmol). The mixture was heated to 80° C. for 1 h, cooled to rt, and filtered through a glass frit. The filter cake was washed 3× with dichloromethane and the organic filtrate was concentrated in vacuo. The resultant residue was subjected to silica gel chromatography eluting with 0-30% EtOAc in hexanes to provide tert-butyl 4-cyano-4-(4-formylpyridin-2-yl)piperidine-1-carboxylate that gave a proton NMR spectra consistent with theory.

Workup

  1. temperaturecooled to rt
  2. filtrationfiltered through a glass frit
  3. washThe filter cake was washed 3× with dichloromethane
  4. concentrationthe organic filtrate was concentrated in vacuo
  5. washeluting with 0-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-44a5770e1a4c4be0b3fd1105feecca58
Source dataset
uspto-grants-2014_06
Patent number
US08754220B2

Reaction notes

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