(Diethylamino)sulfur trifluoride → HCID 118207444, Verbindung

HRID 1507222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1507222
O[C@H:2]1[C@H:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1.CCN(S(F)(F)[F:28])CC>C(Cl)Cl>[F:28][C@H:2]1[C@H:7]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:6][CH2:5][N:4]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:3]1

Komponenten

4

Edukt 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 24820608Tert-butyl (3S,4S)-3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate

Produkt 1

HCID 118207444HCID 118207444, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (3S,4S)-tert-butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate (400 mg, 1.36 mmol, the first eluting enantiomer E-1 from step E) in DCM (5 mL) cooled to 0° C. was added dropwise DAST (0.54 mL, 4.1 mmol) over 10 min. The mixture was allowed to warm up to rt and was stirred for 2 h. The reaction was slowly quenched with 50 mL of a 10% aqueous sodium bicarbonate solution and extracted four times with 50 mL of DCM. The combined organic layers were washed with 75 mL of brine, dried, and concentrated under vacuum to yield 390 mg of (3S,4S)-tert-butyl 3-fluoro-4-(4-hydroxyphenyl)piperidine-1-carboxylate which was used without further purification. LCMS (Method Q) RT 0.92 min, m/z 240.1 (M+H+).

Aufarbeitung

  1. customThe reaction was slowly quenched with 50 mL of a 10% aqueous sodium bicarbonate solution
  2. extractionextracted four times with 50 mL of DCM
  3. washThe combined organic layers were washed with 75 mL of brine
  4. customdried
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-29e17b7b3f3e48faacfdf92390431a1b
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221796B2

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