Methanesulfonyl chloride → HCID 22248366, Verbindung

HRID 890029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 890029
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:16]#[N:17])([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>O1CCCC1.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:16]#[N:17])([CH2:14][O:15][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 222486071-Boc-4-cyano-4-(hydroxymethyl)piperidine

Produkt 1

HCID 22248366HCID 22248366, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

After dissolving 537 mg of 1-(tert-butoxycarbonyl)-4-cyano-4-(hydroxymethyl)piperidine in 100 ml of tetrahydrofuran, 0.4 ml of triethylamine was added and the solution was cooled to 0° C. 0.2 ml of methanesulfonyl chloride was added and the mixture was stirred overnight at room temperature. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. After adding water to the residue, extraction was performed with ethyl acetate. The organic layer was washed with water and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (799 mg, 100% yield).

Aufarbeitung

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionAfter adding water
  5. extractionto the residue, extraction
  6. washThe organic layer was washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b103556736ea4333b0ad675f61ae6d8c
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995144B2

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