Trifluoroacetic acid → Piperidine-4-carbothioic acid S-phenyl ester

HRID 713444

Reaktionsgleichung

Reaktionsgleichung von HRID 713444
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([S:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:17]1([S:16][C:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:15])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 893758004-Phenylsulfanylcarbonyl-piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 89389269Piperidine-4-carbothioic acid S-phenyl esterAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-phenylsulfanylcarbonyl-piperidine-1-carboxylic acid tert-butyl ester (1.11 g, 3.45 mmol) in dichloromethane (10 mL) was then added TFA (2 mL) the reaction was then stirred at 25° C. for 2.5 hours and the solvent was removed under vacuum and the crude material was co-evaporated 3 times with dichloromethane to afford the title compound (750 mg, 3.31 mmol). The crude material was used directly in the next step without subsequent purification. MS (ESI) m/z 221.8 (M+H+); HPLC (Insertsil ODS3 100×3 mm C-18 column: mobile phase: 5-95% acetonitrile/water with 0.1% TFA, at 1 mL/min over 7.75 min.), t=1.29 min.

Aufarbeitung

  1. customthe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-28638420b41f49749a8740749c6c0f5e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181266B2

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