Triacetoxyperiodinane → tert-Butyl (6-oxospiro[3.3]heptan-2-yl)carbamate

HRID 1749516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749516
[OH:1][CH:2]1[CH2:16][C:4]2([CH2:7][CH:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:5]2)[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:1]=[C:2]1[CH2:3][C:4]2([CH2:7][CH:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:5]2)[CH2:16]1

Komponenten

5

Edukt 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 253240582-(Boc-amino)-6-hydroxyspiro(3.3)heptane

Produkt 1

HCID 39872257tert-Butyl (6-oxospiro[3.3]heptan-2-yl)carbamateAusbeute 80,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (6-hydroxyspiro[3.3]heptan-2-yl)carbamate (1.00 g, 4.40 mmol) in DCM (10 mL) was added Dess-Martin periodinane (2.80 g, 6.60 mmol) at ˜0° C. to 10° C. The resulting reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was treated with aqueous sodium bicarbonate and extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. Concentration under vacuum gave the crude product, which was purified by silica gel column chromatography (22% ethyl acetate in petroleum ether) to afford the title compound (800 mg, 3.55 mmol, 80% yield) as a pale yellow solid. MS (ESI) m/z 226.1 [M+H]+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. extractionextracted with DCM
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationConcentration under vacuum
  7. customgave the crude product, which
  8. customwas purified by silica gel column chromatography (22% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-aacccbede0bc4938b40f76b78f9a125c
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156798B2

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