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2-Bromopropane → HCID 57129610, Verbindung

HRID 2299619
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2299619
[OH-].[K+].[OH:3][C:4]1[CH:40]=[CH:39][C:7]2[CH2:8][CH2:9][CH2:10][CH:11]([N:13]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:14][C@H:15]([O:24][Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27])[CH2:16][O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][C:6]=2[CH:5]=1.[CH:41](Br)([CH3:43])[CH3:42].C(=O)([O-])O.[Na+]>CS(C)=O>[CH:41]([O:3][C:4]1[CH:40]=[CH:39][C:7]2[CH2:8][CH2:9][CH2:10][CH:11]([N:13]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:14][C@H:15]([O:24][Si:25]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:30][CH3:31])[CH2:16][O:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:12][C:6]=2[CH:5]=1)([CH3:43])[CH3:42]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 63582-BromopropaneHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 57157362HCID 57157362, Verbindung

Produkt 1

HCID 57129610HCID 57129610, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Versuchsvorschrift

Under nitrogen, to dimethylsulfoxide (3 ml) was added potassium hydroxide (31 mg) at room temperature, and the suspension was stirred at the same temperature for 1 hour. To this one were added N-(3-hydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-[(2S)-3-phenoxy-2-(triethylsilyloxy)propyl]-tert-butoxycarbonylamine (150 mg) and isopropyl bromide (78 μl), and the mixture was stirred at room temperature for 3 hours. The resulting mixture was poured into aqueous 10% sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate =20:1) to give N-(3-isopropoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-[(2S)-3-phenoxy-2-(triethylsilyloxy)propyl]-tert-butoxycarbonylamine (96 mg).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate =20:1)

Quellen und Nachweise

ORD-Eintrag
ord-d1ed423f00ca4be8b74bba37b4135a90
Quelldatensatz
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06495546B1

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