Water → 1-(Diphenylmethyl)-3-(pentylsulfonyl)azetidine

HRID 82962

Reaktionsgleichung

Reaktionsgleichung von HRID 82962
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:11][CH:10]([S:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:24]S(O)(=O)=O.OOS([O-])=O.[K+].C([O-])(O)=O.[Na+].[OH2:40]>CO>[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([S:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:24])=[O:40])[CH2:9]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

7

Edukt 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 671546441-(Diphenylmethyl)-3-(pentylthio)azetidine

Produkt 1

HCID 671545941-(Diphenylmethyl)-3-(pentylsulfonyl)azetidineAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-(diphenylmethyl)-3-(pentylthio)azetidine (228 mg, 0.70 mmol; which may be prepared as described in Step 2) in methanol (6.3 mL) and water (6.3 mL) was added H2SO4 1N (0.7 mL). The reaction mixture was stirred for 10 minutes, then oxone (1.08 g, 1.75 mmol) was added and the mixture stirred at room temperature for 12 h. A solution of saturated NaHCO3 (5 mL) was added and the mixture extracted with ethyl acetate. The two layers were separated and the organic washed with brine, dried over Na2SO4, filtered and concentrated. The crude was then purified on column chromatography (pentane/EtOAc, 100/0 then 90/10) to give the title product (75 mg, 30%) as a pale yellow oil. The less pure fraction (N-oxide) can be recycled in hydrogenolysis conditions.

Aufarbeitung

  1. stirringthe mixture stirred at room temperature for 12 h
  2. extractionthe mixture extracted with ethyl acetate
  3. customThe two layers were separated
  4. washthe organic washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude was then purified on column chromatography (pentane/EtOAc, 100/0

Quellen und Nachweise

ORD-Eintrag
ord-f630a1a4c82748fa9814874697e5c059
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846711B2

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