Bis(acetoxy)iodobenzene → HCID 86731562, compound

HRID 1430578Notes

Reaction equation

HRID 1430578 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][N:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:17]2[N:21]=[CH:20][CH:19]=[N:18]2)=[O:10])[C@H:6]([CH3:22])[CH2:5][CH2:4]1.C(OC1C(OC(=O)C)=C(I)C=CC=1)(=O)C>ClCCl>[CH3:22][C@H:6]1[N:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:17]2[N:21]=[CH:20][CH:19]=[N:18]2)=[O:10])[CH2:8][C@H:3]([CH:2]=[O:1])[CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 21865429Bis(acetoxy)iodobenzeneHCID 59396049HCID 59396049, compound

Product 1

HCID 86731562HCID 86731562, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(2R,5R)-5-(hydroxymethyl)-2-methylpiperidin-1-yl][2-(2H-1,2,3-triazol-2-yl)phenyl]methanone (0.76 g, 2.5 mmol) in dichloromethane (25 mL) was added (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl (0.06 g, 0.38 mmol) and diacetoxyiodobenzene (0.81 g, 2.5 mmol). The mixture was stirred at ambient temperatures for 18 hours, then washed with aqueous sodium thiosulfite (1×30 mL) and aqueous sodium bicarbonate (2×50 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography eluting with 0-2% methanol in dichloromethane to provide (3R,6R)-6-methyl-1-{[2-(2H-1,2,3-triazol-2-yl)phenyl]carbonyl}piperidine-3-carbaldehyde as a clear oil.

Workup

  1. washwashed with aqueous sodium thiosulfite (1×30 mL) and aqueous sodium bicarbonate (2×50 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluting with 0-2% methanol in dichloromethane

Sources & evidence

ORD record
ord-d2283151566944deab3aec0f1cc18c06
Source dataset
uspto-grants-2015_01
Patent number
US08940898B2

Reaction notes

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