Methanesulfonyl chloride → 1-Methyl-2-oxo-3-piperidinyl methanesulfonate

HRID 622630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 622630
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][N:7]1[CH2:12][CH2:11][CH2:10][CH:9]([OH:13])[C:8]1=[O:14]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][S:2]([O:13][CH:9]1[CH2:10][CH2:11][CH2:12][N:7]([CH3:6])[C:8]1=[O:14])(=[O:4])=[O:3]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 144568943-Hydroxy-1-methylpiperidin-2-one

Produkt 1

HCID 144568951-Methyl-2-oxo-3-piperidinyl methanesulfonateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Methanesulfonyl chloride (0.8 ml., 0.01 mole) was added dropwise to a stirred solution of 1-methyl-2-oxo-3-piperidinol (1.29 g, 0.01 mole) and 4-dimethylaminopyridine (2.44 g., 0.02 mole), in 50 ml. methylene chloride at 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 15 min. and at 25° C. for 2.5 hours. The reaction mixture was then washed with 50 ml. saturated aqueous sodium chloride solution containing 6.8 ml. of 6N aqueous hydrochloric acid solution, dried over anhydrous sodium sulfate and concentrated in vacuo to a thick oil of the title compound (1.8 g., 87% yield). NMR (CDCl3): 1.6-2.37 (c, 4H); 2.96 (s, 3H); 3.1-3.4 (c) and 3.24 (s) (total 5H); and 4.9 (m, 1H)ppm.

Aufarbeitung

  1. customat 0° C.
  2. washThe reaction mixture was then washed with 50 ml
  3. additionsaturated aqueous sodium chloride solution containing 6.8 ml
  4. dry with materialof 6N aqueous hydrochloric acid solution, dried over anhydrous sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-58db7a1c6e7446e784feaf79cbd0c6ab
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04772597

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