Cyclobutanone → 6-Cyclobutyl-2-[4-(methylsulfonyl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

HRID 1364157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1364157
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:20]=[C:19]3[C:13]([CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)=[N:12]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:21]1(=O)[CH2:24][CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH:21]1([N:16]2[CH2:17][CH2:18][C:19]3=[CH:20][N:11]([C:8]4[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=4)[N:12]=[C:13]3[CH2:14][CH2:15]2)[CH2:24][CH2:23][CH2:22]1

Komponenten

7

Edukt 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 669307912-[4-(Methylsulfonyl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

Produkt 1

HCID 160488376-Cyclobutyl-2-[4-(methylsulfonyl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-[4-(methylsulfonyl)phenyl]-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine (may be prepared as described in Description 38) (4 mg, 0.014 mmol) in dichloromethane (2 ml) was added cyclobutanone (7 mg, 0.096 mmol) and acetic acid (1 drop). The resulting mixture was stirred at room temperature, under argon, for 20 minutes. Sodium triacetoxyborohydride (20 mg, 0.096 mmol) was added and stirring continued overnight. The resulting reaction mixture was diluted with methanol and purified by SCX, eluting with methanol and then with 2M ammonia/methanol. The basic fractions were combined and solvent evaporated in vacuo to afford the title compound (E28). MS (ES+) m/e 346 [M+H]+.

Aufarbeitung

  1. stirringstirring continued overnight
  2. customThe resulting reaction mixture
  3. custompurified by SCX
  4. washeluting with methanol
  5. customsolvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-030525f36bb141cfa495dc65248354e2
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888347B2

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