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Methanol → methyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylate

HRID 397670
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 397670
CO.Cl.[CH3:4]N(C)CCCN=C=NCC.[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]2[C:31]([OH:33])=[O:32])(=[O:24])=[O:23])=[CH:18][CH:17]=1>CN(C)C1C=CN=CC=1.ClCCl>[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]2[C:31]([O:33][CH3:4])=[O:32])(=[O:24])=[O:23])=[CH:18][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 887MethanolHCID 768662(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 57268970methyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylateAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

4-Dimethylaminopyridine (61 mg), methanol (45 μl) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (192 mg) were added to a solution of (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylic acid (287 mg) [see Preparation 38] in dichloromethane (6 ml). The reaction mixture was stirred at room temperature for 56 hours after which time it was diluted with dichloromethane and washed with 1N aqueous hydrochloric acid solution followed by saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 90:10 changing to 50:50, by volume, hexane:ethyl acetate, to afford methyl (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylate (239 mg) as an oil.

Aufarbeitung

  1. washwashed with 1N aqueous hydrochloric acid solution
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. customthe solvent removed under reduced pressure
  4. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 90:10 changing to 50:50, by volume, hexane

Quellen und Nachweise

ORD-Eintrag
ord-9a4492d48a8047608dbd2a1c2e630d4f
Quelldatensatz
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06610707B1

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