Triacetoxyperiodinane → Benzyl 3-formylpiperidine-1-carboxylate

HRID 48474

Reaktionsgleichung

Reaktionsgleichung von HRID 48474
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C@@H:13]([CH2:17][OH:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH:17]=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 6932120benzyl (3R)-3-(hydroxymethyl)piperidine-1-carboxylate

Produkt 1

HCID 9899653Benzyl 3-formylpiperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirring, 0° C. solution of 0.303 g (1.20 mmol) of 3-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester (8) in CH2Cl2 (4.0 mL) was added 0.630 g (1.44 mmol) of Dess-Martin periodinane, and the solution was stirred under N2. When the reaction was complete by TLC (about 30 min.), the reaction was concentrated, and then Et2O was added. After standing for about 15 min., the reaction was filtered through Celite wet with Et2O, rinsed with Et2O, and concentrated. The crude reaction was purified by column chromatography (florisil®, 100-200 mesh, 2:1 Hexane: EtOAc) to achieve pure 9.

Aufarbeitung

  1. customwas complete by TLC (about 30 min.)
  2. concentrationthe reaction was concentrated
  3. additionEt2O was added
  4. filtrationthe reaction was filtered through Celite wet with Et2O
  5. washrinsed with Et2O
  6. concentrationconcentrated
  7. customThe crude reaction
  8. customwas purified by column chromatography (florisil®, 100-200 mesh, 2:1 Hexane: EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-b2a037f8cccc4e88ae1cfed235e1c2c0
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703508B2

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