Toluene → t-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-1H-pyrrol-1-yl)ethyl)-2-phenyl-1,3,2-dioxaborinan-4-yl)acetate

HRID 1925640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1925640
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][C:11](=O)[CH:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[NH2:30][CH2:31][CH2:32][C@H:33]1[O:38][B:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[O:36][C@@H:35]([CH2:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:34]1.C(O)(=O)C(C)(C)C>C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:30]([CH2:31][CH2:32][C@H:33]3[O:38][B:37]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[O:36][C@@H:35]([CH2:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:34]3)[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][C:9]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 6417Pivalic acidHCID 11449985t-butyl 2-((4R,6R)-6-(2-aminoethyl)-2-phenyl-1,3,2-dioxaborinan-4-yl)acetateHCID 147571731-(4-Fluorophenyl)-5-methyl-2-phenylhexane-1,4-dione

Produkt 1

HCID 58112769t-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-1H-pyrrol-1-yl)ethyl)-2-phenyl-1,3,2-dioxaborinan-4-yl)acetateAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

To a nitrogen-filled flask, 126 g of 1-(4-fluorophenyl)-5-methyl-2-phenyl-1,4-hexanedione, 2.5 L of toluene, 41 ml of triethylamine, 160 g of t-butyl 2-((4R,6R)-6-(2-aminoethyl)-2-phenyl-1,3,2-dioxaborinan-4-yl)acetate and 33 ml of pivalic acid were added. The mixture was heated to reflux with stirring for 14 hours while removing water with a Dean-Stark trap. The reaction mixture was cooled slowly to 20-25° C. and washed with purified water, and the organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure, thus obtaining 194 g of the title compound as yellow oil.

Aufarbeitung

  1. additionTo a nitrogen-filled flask
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. customwhile removing water with a Dean-Stark trap
  5. washwashed with purified water
  6. customthe organic layer was separated
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3749f65dcc8249c2a36b9a5ef9cb809a
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178697B2

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