Boron tribromide → cis-(+/-)-5-Bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-6-ol

HRID 257194

Reaction equation

HRID 257194 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11]C)[N:7]([CH3:13])[C@H:6]1[N:14]([CH3:17])[CH2:15][CH2:16][C@@:5]21[CH3:18].B(Br)(Br)Br>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[N:7]([CH3:13])[C@H:6]1[N:14]([CH3:17])[CH2:15][CH2:16][C@@:5]21[CH3:18]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67752673cis-(+/-)-5-Bromo-1,2,3,3a,8,8a-hexahydro-6-methoxy-1,3a,8-trimethylpyrrolo[2,3-b]indol

Product 1

HCID 67753116cis-(+/-)-5-Bromo-1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethylpyrrolo[2,3-b]indol-6-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

cis-(±)-5-Bromo-1,2,3,3a,8,8a-hexahydro-6-methoxy-1,3a,8-trimethylpyrrolo[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. Na2CO3 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.

Workup

  1. customThe mixture was quenched with aq. Na2CO3 and aq. NaHCO3 until basic at 0° C
  2. customThe organic layer was dried
  3. customevaporated to a foam (10 g)

Sources & evidence

ORD record
ord-e45d5551c0c945c89bbc5412fec3b04f
Source dataset
uspto-grants-1993_11
Patent number
US05260452

Linked notes

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