Triacetoxyperiodinane → tert-Butyl (3-oxocyclopentyl)carbamate

HRID 1500893Notes

Reaction equation

HRID 1500893 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 23568739tert-Butyl (3-hydroxycyclopentyl)carbamate

Product 1

HCID 53427213tert-Butyl (3-oxocyclopentyl)carbamateYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl(3-hydroxycyclopentyl)carbamate (800 mg, 3.98 mmol) and Dess-martin reagent (3.6 g, 8.15 mmol) in DCM (20 mL) was stirred at RT overnight. And then, the reaction was quenched by addition of sat. aqueous solution of NaHCO3 and sat. aqueous solution of Na2SO3. The resulting mixture was extracted with DCM (20 mL×3). The combined organic layers were dried over Na2SO4, and then concentrated in vacuo. The residue was purified by silica-gel chromatography to afford tert-butyl(3-oxocyclopentyl)carbamate as a white solid (730 mg).

Workup

  1. customAnd then, the reaction was quenched by addition of sat. aqueous solution of NaHCO3 and sat. aqueous solution of Na2SO3
  2. extractionThe resulting mixture was extracted with DCM (20 mL×3)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica-gel chromatography

Sources & evidence

ORD record
ord-97abb1b1c9a84484810a380806095b77
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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