Dimethyl Sulfoxide → 5-Benzyl-1-oxa-5-azaspiro[2.5]octane

HRID 720043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720043
[H-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][C:12](=[O:16])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:17]S(C)=O>C1COCC1>[CH2:3]([N:10]1[CH2:15][CH2:14][CH2:13][C:12]2([O:16][CH2:17]2)[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 679Dimethyl Sulfoxide2×HCID 24758Sodium hydrideHCID 966503-Piperidinone, 1-(phenylmethyl)-

Produkt 1

HCID 137207665-Benzyl-1-oxa-5-azaspiro[2.5]octaneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium hydride (583 mg, 14.6 mmol) in DMSO (6 mL) was heated to 55° C. for 1 h. The reaction mixture is cooled to 0° C. and Me3SI (3 g, 14.62 mmol) dissolved in THF (9.8 mL) was added dropwise. 1-Benzyl-piperidine-3-one (1.5 g, 6.64 mmol) dissolved in DMSO (10 mL) was added 15 minutes later. After completion of addition the reaction proceded at RT. After 30 min. the reaction was quenched with water. The aqueous layer was extracted with hexanes. Combined organic layers were dried over Na2SO4 and concentrated. The crude material was purified using silica gel chromatography (9:1 DCM:hexanes in 2 M ammonia in EtOH) to yield 5-benzyl-1-oxa-5-aza-spiro[2.5]octane (960 mg, 71%). MH+ (204).

Aufarbeitung

  1. additionwas added dropwise
  2. additionwas added 15 minutes later
  3. additionAfter completion of addition the reaction
  4. customproceded at RT
  5. customAfter 30 min. the reaction was quenched with water
  6. extractionThe aqueous layer was extracted with hexanes
  7. dry with materialCombined organic layers were dried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude material was purified

Quellen und Nachweise

ORD-Eintrag
ord-af85d8f5f543434eb12d0ff8dc255dae
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132551B2

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