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Hydrochloric Acid → HCID 68501783, Verbindung

HRID 1714052
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1714052
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:35]([O:37][CH3:38])=[O:36])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([C:22](=O)[C@H:23]4[CH2:27][CH2:26][CH2:25][N:24]4[CH3:28])[CH2:18][C:17]4[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B.C1COCC1.Cl>C1COCC1.CO.CCOC(C)=O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:35]([O:37][CH3:38])=[O:36])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([CH2:22][C@H:23]4[CH2:27][CH2:26][CH2:25][N:24]4[CH3:28])[CH2:18][C:17]4[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 68506071HCID 68506071, Verbindung

Produkt 1

HCID 68501783HCID 68501783, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×
HCID 8028
Tetrahydrofuran
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of methyl 14-cyclohexyl-3-fluoro-6-(1-methyl-D-prolyl)-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate in THF (0.02 M), 3×5 eq of BH3.THF (1 M solution in THF) were added sequentially over a period of 48 h. The solution was allowed to stir at RT and monitored until no starting material was visible by RP-LC-MS. MeOH (0.02 M) and a 1.25 M solution of HCl in MeOH (0.24 M) were added carefully and the mixture heated at reflux for 2 h. The volume of the solution was reduced in vacuo, before diluting with EtOAc. The organic phase was washed with aqueous NaHCO3 solution and brine, before being dried over Na2SO4, filtered and the solvent evaporated in vacuo to afford the title compound. The crude was used in the next step without further purification (quant); MS (ES+) m/z 504 (M+H)+.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 h
  3. washThe organic phase was washed with aqueous NaHCO3 solution and brine
  4. dry with materialbefore being dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5ab9e32548b34332bfd21306b002d321
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07795247B2

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