Water → (3-(tert-Butoxycarbonyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)boronic acid

HRID 1715003

Reaktionsgleichung

Reaktionsgleichung von HRID 1715003
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:26]=[CH:25][C:12]3[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17][C:11]=3[CH:10]=2)[O:3]1.I([O-])(=O)(=O)=O.[Na+].C([O-])(=O)C.[NH4+].O>CC(C)=O>[CH3:24][C:21]([O:20][C:18]([N:15]1[CH2:14][CH2:13][C:12]2[CH:25]=[CH:26][C:9]([B:4]([OH:5])[OH:3])=[CH:10][C:11]=2[CH2:17][CH2:16]1)=[O:19])([CH3:22])[CH3:23]

Komponenten

6

Edukt 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 23667635Sodium periodateHCID 57505869tert-Butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-benzo[d]azepine-3-carboxylate

Produkt 1

HCID 57440296(3-(tert-Butoxycarbonyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)boronic acidAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

1,1-Dimethylethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate (E264, Step 1) (1.60 g, 4.29 mmol) was dissolved in acetone (25 ml), treated with sodium periodate (2.75 g, 12.9 mmol), ammonium acetate (0.73 g, 9.44 mmol) and water (25 ml) and the resulting mixture was stirred for 18 hours at room temperature. The acetone was removed by evaporation in vacuo and the remaining water layer was extracted with ethyl acetate and dichloromethane. The organic layers were combined, dried under magnesium sulfate and evaporated in vacuo to give the title compound (1.06 g); MS (ES+) m/e 192 [(M+H)—CO2tBu]+.

Aufarbeitung

  1. customThe acetone was removed by evaporation in vacuo
  2. extractionthe remaining water layer was extracted with ethyl acetate and dichloromethane
  3. customdried under magnesium sulfate
  4. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f79ba70ff3d44ca4bf7792f2874a1ef6
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799773B2

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