Ethanol → 1-(4-Ethoxycarbonyl-1,3-thiazol-2-yl)4-methanesulfonyloxypiperidine

HRID 891568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891568
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:11]2[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13][CH2:12]2)[S:9][CH:10]=1)=[O:5])[CH3:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(N(CC)CC)C.C(O)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:11]2[CH2:12][CH2:13][CH:14]([O:17][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:15][CH2:16]2)[S:9][CH:10]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22242823Ethyl 2-(4-hydroxypiperidin-1-yl)thiazole-4-carboxylate

Produkt 1

HCID 865908511-(4-Ethoxycarbonyl-1,3-thiazol-2-yl)4-methanesulfonyloxypiperidineAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)-4-hydroxypiperidine (128 mg, 0.50 mmol) (obtained as described in Reference Example 13(2)) in methylene chloride (6.5 ml) was added methanesulfonyl chloride (0.043 ml, 0.56 mmol) and triethylamine (0.084 ml, 0.60 mmol) in an ice bath. The reaction mixture was brought to room temperature in 10 minutes and then stirred for 30 minutes. After checking the completion of the reaction, ethanol (1 ml) was added thereto in an ice bath and then the reaction mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was recrystallized from a solution of ethyl acetate:n-hexane (5:1) to afford 1-(4-ethoxycarbonyl-1,3-thiazol-2-yl)4-methanesulfonyloxypiperidine (81.0 mg, yield 49%) as a white solid.

Aufarbeitung

  1. additionwas added
  2. stirringin an ice bath and then the reaction mixture was stirred for 30 minutes
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was recrystallized from a solution of ethyl acetate:n-hexane (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-deeeaf3e388342b5bdd93e9333f99c92
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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