Reaktion #1864

ord-81f17a5f0c63408184ecd6ae2c164668

Reaktionsgleichung

COc1cc2c(cc1Br)[C@]1(C)CCN(C)[C@@H]1N2C
cis-(±)-5-Bromo-1,2,3,3a,8,8a-hexahydro-6-methoxy- 1,3a,8-trimethyl-pyrrolo[2,3-b]indole
BrB(Br)Br
BBr3
CN1CC[C@@]2(C)c3cc(Br)c(O)cc3N(C)[C@@H]12
cis-(±)-5-Bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-6-ol

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe mixture was quenched with aq. Na2 CO3 and aq. NaHCO3 until basic at 0° C
  2. 2
    SonstigeThe organic layer was dried
  3. 3
    Sonstigeevaporated to a foam (10 g)

Vorschrift

cis-(±)-5-Bromo-1,2,3,3a,8,8a-hexahydro-6-methoxy- 1,3a,8-trimethyl-pyrrolo[2,3-b]indole (11 g) was dissolved in dry DCM (200 ml) and added dropwise at 0° C. to a stirred solution of BBr3 in DCM (300 ml). The mixture was warmed to room temperature and stirred overnight under nitrogen. The mixture was quenched with aq. Na2 CO3 and aq. NaHCO3 until basic at 0° C. The organic layer was dried and evaporated to a foam (10 g). The IR, NMR and Mass Spectra confirmed the purity and identity of this product.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726323uspto-grants-1998_03