Cyclobutanone → 4-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-methyl-3-(methyloxy)benzamide

HRID 645887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 645887
[CH3:1][NH:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:21]=[CH:20][C:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][C:13]=3[CH:12]=2)=[C:6]([O:22][CH3:23])[CH:5]=1.[C:25]1(=O)[CH2:28][CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C.CO>[CH:25]1([N:17]2[CH2:16][CH2:15][C:14]3[CH:20]=[CH:21][C:11]([O:10][C:7]4[CH:8]=[CH:9][C:4]([C:3]([NH:2][CH3:1])=[O:24])=[CH:5][C:6]=4[O:22][CH3:23])=[CH:12][C:13]=3[CH2:19][CH2:18]2)[CH2:28][CH2:27][CH2:26]1

Komponenten

7

Edukt 3

HCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 57440300N-Methyl-3-(methyloxy)-4-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yloxy)benzamide

Produkt 1

HCID 103176494-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-N-methyl-3-(methyloxy)benzamideAusbeute 21,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-Methyl-3-(methyloxy)-4-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yloxy)benzamide (E264, Step 6) (78 mg, 0.24 mmol) was dissolved in dry dichloromethane (5 ml), treated with cyclobutanone (0.04 ml, 0.48 mmol) and acetic acid (1 drop) and the resulting mixture stirred for 15 minutes. Sodium triacetoxyborohydride (102 mg, 0.48 mmol) was added and the mixture stirred for 30 minutes. The mixture was diluted with methanol and applied to a SCX column eluting with methanol and then a mixture of 0.880 ammonia/methanol (1:9). The basic fractions were combined and concentrated in vacuo. The resulting residue was purified by column chromatography eluting with a mixture of ammonia:methanol:dichloromethane (0.5:4.5:95.880) to afford the title compound (20 mg); MS (ES+) m/e 381 [M+H]+.

Aufarbeitung

  1. stirringthe mixture stirred for 30 minutes
  2. washeluting with methanol
  3. additiona mixture of 0.880 ammonia/methanol (1:9)
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography
  6. washeluting with a mixture of ammonia:methanol:dichloromethane (0.5:4.5:95.880)

Quellen und Nachweise

ORD-Eintrag
ord-a87ba8c874904802bbbfc3f700d8e02f
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07704994B2

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