4-[3-(Trifluoromethyl)phenyl]-4-piperidinol → 1-(2-Methyl-7,8-dihydro-1,6,9-trioxa-3-aza-cyclopenta[a]naphthalen-8-ylmethyl)-4-[3-(trifluoromethyl)phenyl]-4-piperidinol

HRID 2414844

Reaktionsgleichung

Reaktionsgleichung von HRID 2414844
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:26][O:25][C:16]3[CH:17]=[CH:18][C:19]4[N:20]=[C:21]([CH3:24])[O:22][C:23]=4[C:15]=3[O:14]2)(=O)=O)=CC=1.[F:27][C:28]([F:43])([F:42])[C:29]1[CH:30]=[C:31]([C:35]2([OH:41])[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH:32]=[CH:33][CH:34]=1>CS(C)=O>[CH3:24][C:21]1[O:22][C:23]2=[C:15]3[C:16](=[CH:17][CH:18]=[C:19]2[N:20]=1)[O:25][CH2:26][CH:13]([CH2:12][N:38]1[CH2:37][CH2:36][C:35]([C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([C:28]([F:27])([F:42])[F:43])[CH:30]=2)([OH:41])[CH2:40][CH2:39]1)[O:14]3

Komponenten

4

Edukt 2

HCID 752554-[3-(Trifluoromethyl)phenyl]-4-piperidinolHCID 11245807(8R)-2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-ylmethyl 4-methylbenzenesulfonate

Produkt 1

HCID 102755481-(2-Methyl-7,8-dihydro-1,6,9-trioxa-3-aza-cyclopenta[a]naphthalen-8-ylmethyl)-4-[3-(trifluoromethyl)phenyl]-4-piperidinol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(8R)-2-Methyl-7,8-dihydro[1,4]dioxino[2,3-g][1,3]benzoxazol-8-ylmethyl 4-methylbenzenesulfonate (0.43 g, 1.14 mmole) and 4-[3-(trifluoromethyl)phenyl]-4-piperidinol (0.84 g, 3.43 mmole) were combined in 10 mL of DMSO under nitrogen. This solution was heated to 80° C. under nitrogen for 4 hours. After completion, the reaction was allowed to cool to room temperature and was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuum. The resulting crude oil was column chromatographed on silica gel using first methylene chloride to remove impurities and then 1% methanol/methylene chloride to elute 0.33 g of the (S)-enantiomer of the title compound, m.p. 148-151° C.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customwas partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuum
  6. customchromatographed on silica gel using first methylene chloride
  7. customto remove impurities
  8. wash1% methanol/methylene chloride to elute 0.33 g of the (S)-enantiomer of the title compound, m.p. 148-151° C.

Quellen und Nachweise

ORD-Eintrag
ord-61d8c17849ec41a780ae47ef11fbf038
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06815448B2

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