Sulfoxonium, trimethyl-, iodide (1:1) → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 854329

Reaktionsgleichung

Reaktionsgleichung von HRID 854329
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[I-].[CH3:16][S+](C)(C)=O.CC(C)([O-])C.[Na+]>C1COCC1.COCCOC>[O:1]1[C:2]2([CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH2:16]1

Komponenten

5

Edukt 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 23676156Sodium t-butoxide

Produkt 1

HCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22732251Tetrahydrofuran dimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (0.50 g, 2.51 mmol) in THF/DME (2:1, 6 mL) at 60° C. was added trimethylsulfoxonium iodide (0.58 g, 2.63 mmol) and sodium t-butoxide (0.25 g, 2.63 mmol). The reaction mixture was stirred at 60° C. for 30 min, cooled to rt and concentrated. Water was added and the mixture was extract with EtOAc twice. The combined organics were dried over Na2SO4, filtered and concentrated. Purification on silica gel (3:1, hexanes:EtOAc) gave tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate as a clear oil that solidified upon standing.

Aufarbeitung

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. additionWater was added
  4. extractionthe mixture was extract with EtOAc twice
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification on silica gel (3:1, hexanes:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-cae21a44277c4849a0103731f1b91da8
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259157B2

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