Acetic Acid → 4-(Trifluoromethyl)benzamide

HRID 1950938

Reaktionsgleichung

Reaktionsgleichung von HRID 1950938
CO[C:3]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15](SC)[C:4]=1[C:5]([NH:7]C1CCCCC1=O)=[O:6].C(O)(=O)C.N1CCCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[F:20][C:19]([F:21])([F:22])[C:17]1[CH:18]=[CH:3][C:4]([C:5]([NH2:7])=[O:6])=[CH:15][CH:16]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 580629692-methoxy-6-methylsulfanyl-N-(2-oxo-cyclohexyl)-4-trifluoromethyl-benzamide2×

Produkt 1

HCID 746844-(Trifluoromethyl)benzamideAusbeute 62,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-Methoxy-6-methylsulfanyl-N-(2-oxo-cyclohexyl)-4-trifluoromethyl-benzamide (intermediate B, 380 mg, 1.05 mmol) was dissolved in 10 mL tetrahydrofurane. Acetic acid (145 mg, 2.4 mmol) and pyrrolidine (97 mg, 1.4 mmol) were added and the reaction mixture was stirred 1 h at room temperature. Sodium triacetoxyborohydride (290 mg, 1.4 mmol) was added and stirring was continued at room temperature overnight. The mixture was extracted with 2N sodium carbonate solution and ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0->140:10:1) yielded cis-2-methoxy-6-methylsulfanyl-N-2-pyrrolidin-1-yl-cyclohexyl)-4-trifluoromethyl-benzamide as a light yellow solid (125 mg, 28%), MS: m/e=417.3 [(M+H)] and trans-2-methoxy-6-methylsulfanyl-N-2-pyrrolidin-1-yl-cyclohexyl)-4-trifluoromethyl-benzamide as a light yellow solid (28 mg, 6%), MS: m/e=417.3 [(M+H)+].

Aufarbeitung

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. extractionThe mixture was extracted with 2N sodium carbonate solution and ethyl acetate
  4. customThe combined organic phases were dried on sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0->140:10:1)

Quellen und Nachweise

ORD-Eintrag
ord-e41d64ac1ba14ed583fb0c1651a4be6f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404673B2

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