Dichloromethane → (E)-3-{[2-(t-Butoxycarbonylamino)-1,3-thiazol-4-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol

HRID 1171722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171722
[BH4-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[S:12][CH:13]=[C:14](/[CH:16]=[C:17]2\[CH2:18][N:19]([C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:21][C:22]\2=[O:23])[N:15]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].ClCCl>C(O)C>[C:3]([O:7][C:8]([NH:10][C:11]1[S:12][CH:13]=[C:14](/[CH:16]=[C:17]2\[CH2:18][N:19]([C:24]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:20][CH2:21][CH:22]\2[OH:23])[N:15]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 23138600(E)-3-{[2-(t-butoxycarbonylamino)-1,3-thiazol-4-yl]methylidene}-1-(triphenylmethyl)piperidin-4-one

Produkt 1

HCID 23138938(E)-3-{[2-(t-Butoxycarbonylamino)-1,3-thiazol-4-yl]methylidene}-1-(triphenylmethyl)piperidin-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Sodium borohydride (0.27 g) was added to a solution of (E)-3-{[2-(t-butoxycarbonylamino)-1,3-thiazol-4-yl]methylidene}-1-(triphenylmethyl)piperidin-4-one (3.1 g) in a mixed solvent of dichloromethane (15 ml) and ethanol (15 ml), while stirring at 0° C. After being stirred at room temperature for 1.5 hours, the mixture was partitioned between water and ethyl acetate. The organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The extract was concentrated under reduced pressure to afford the title compound as a yellow amorphous solid in a quantitative yield.

Aufarbeitung

  1. stirringAfter being stirred at room temperature for 1.5 hours
  2. customthe mixture was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe extract was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0cfddc6497c2413d8f2267304c6f7b3c
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829580B2

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