1,2-Dichloroethane → 5-(trifluoromethyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione hydrochloride

HRID 12756

Reaktionsgleichung

Reaktionsgleichung von HRID 12756
[F:1][C:2]([F:16])([F:15])[C:3]1[C:4](=[O:14])[NH:5][C:6](=[O:13])[N:7]([CH2:9][CH2:10][CH:11]=O)[CH:8]=1.[F:17][C:18]([F:32])([F:31])[C:19]1[CH:24]=[CH:23][C:22]([C@:25]23[CH2:30][C@H:29]2[CH2:28][NH:27][CH2:26]3)=[CH:21][CH:20]=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:51]CCCl>C(OCC)(=O)C>[ClH:51].[F:1][C:2]([F:16])([F:15])[C:3]1[C:4](=[O:14])[NH:5][C:6](=[O:13])[N:7]([CH2:9][CH2:10][CH2:11][N:27]2[CH2:28][C@H:29]3[C@:25]([C:22]4[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:32])[F:31])=[CH:24][CH:23]=4)([CH2:30]3)[CH2:26]2)[CH:8]=1

Komponenten

7

Edukt 5

HCID 111,2-Dichloroethane2×HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 589941853-(5-Trifluoromethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-propionaldehydeHCID 59337591(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hexane

Produkt 1

HCID 866159515-(trifluoromethyl)-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione hydrochlorideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-(5-trifluoromethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-propionaldehyde (Prep21, 0.05 g, 0.21 mmol) in DCE (1 mL), (1S,5R)-1-(4-trifluoromethyl-phenyl)-3-aza-bicyclo[3.1.0]hexane (Prep4, 0.08 g, 0.35 mmol) in DCE (1 mL), AcOH (20 μl, 0.36 mmol) and NaBH(AcO)3 (0.09 g, 0.42) were added and the mixture was stirred at room temperature overnight. Ethyl acetate was added and the solution washed with aqueous saturated NaHCO3. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with DCM-MeOH—NH4OH (97-3-1) to give the title compound (0.04 mg, 51% yield) as a free base.

Aufarbeitung

  1. washthe solution washed with aqueous saturated NaHCO3
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated
  4. customThe crude was purified by flash chromatography with DCM-MeOH—NH4OH (97-3-1)

Quellen und Nachweise

ORD-Eintrag
ord-97bae88de57f4bc1aa41a5f634eb98c9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727988B2

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