Triphenylphosphine → Ammonia

HRID 12649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 12649
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@:9]23[CH2:14][C@H:13]2[CH2:12][N:11]([CH2:15][CH2:16][CH2:17]O)[CH2:10]3)=[CH:5][CH:4]=1.[C:21]1([C:27]([N:29]2[C:34](=[O:35])[CH:33]=[CH:32][NH:31][C:30]2=[O:36])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCOCC1>[NH3:11].[C:21]1([C:27]([N:29]2[C:34](=[O:35])[CH:33]=[CH:32][N:31]([CH2:17][CH2:16][CH2:15][N:11]3[CH2:12][C@H:13]4[C@:9]([C:6]5[CH:7]=[CH:8][C:3]([C:2]([F:20])([F:1])[F:19])=[CH:4][CH:5]=5)([CH2:14]4)[CH2:10]3)[C:30]2=[O:36])=[O:28])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 5695133-BenzoyluracilHCID 5462977Diethyl azodicarboxylateHCID 593375943-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-propanol

Produkt 2

HCID 222AmmoniaHCID 589941983-(phenylcarbonyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}-1-propanol (Prep5, 51 mg), 3-(phenylcarbonyl)-2,4(1H,3H)-pyrimidinedione (39 mg, prepared according to the procedure reported in J. Chem. Soc., Perkin Trans. 1, 2827 (1998)) and PPh3 (140 mg) in dry dioxane at 110° C., DEAD (40% solution in toluene, 0.243 mL) was added dropwise. After 3 hours the mixture was concentrated under reduced pressure. The crude product was purified by a silica SPE cartridge (10 g) eluting with DCM/MeOH from 100/0 to 95/5 followed by a SCX cartridge (eluting with MeOH and then NH3 0.3M in methanol) to give the title compound as a colourless oil (35 mg).

Aufarbeitung

  1. concentrationAfter 3 hours the mixture was concentrated under reduced pressure
  2. customThe crude product was purified by a silica SPE cartridge (10 g)
  3. washeluting with DCM/MeOH from 100/0 to 95/5
  4. washeluting with MeOH

Quellen und Nachweise

ORD-Eintrag
ord-bf261ed710fe4fe4af6a038ad9a8bcf1
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

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