Triacetoxyperiodinane → 7-Oxo-azepane-2-carbaldehyde

HRID 1710393Notes

Reaction equation

HRID 1710393 reaction equation
[OH:1][CH2:2][CH:3]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>ClCCl>[O:10]=[C:8]1[NH:9][CH:3]([CH:2]=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 214467037-(Hydroxymethyl)azepan-2-one2×

Product 1

HCID 197764117-Oxo-azepane-2-carbaldehydeYield 36.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

750 mg of 7-hydroxymethyl-azepan-2-on (compound F1) are dissolved in 85 ml of dichloromethane under an atmosphere of dry nitrogen. Subsequently, 2.22 g of triacetoxy periodinane (Dess-Martin reagent) are added at room temperature and stirring is continued for further 3 hours. Thereafter, the suspension is evaporated to dryness to yield 2.65 g of crude material. The crude product is purified by chromatography (eluent gradient: cyclohexane/50-100 vol. % ethyl acetate) to afford 272 mg of the title compound as a colorless, waxy solid. ESI-MS: 140.1 (MH+). TLC: Rf=0.60 (dichloromethane/ethanol 10:1 parts by volume).

Workup

  1. customThereafter, the suspension is evaporated to dryness
  2. customto yield 2.65 g of crude material
  3. customThe crude product is purified by chromatography (eluent gradient: cyclohexane/50-100 vol. % ethyl acetate)

Sources & evidence

ORD record
ord-65235c54ea99409cb5c299f81ee91a9f
Source dataset
uspto-grants-2010_09
Patent number
US07790710B2

Reaction notes

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