Methanol → HCID 67877130, compound

HRID 2082322Notes

Reaction equation

HRID 2082322 reaction equation
B(Br)(Br)[Br:2].[N:5]12[CH2:12][CH2:11][CH:8]([CH2:9][CH2:10]1)[C@H:7]([N:13]1[CH:28]=[CH:27][C:16]3[N:17]([CH3:26])[C:18]4[CH:19]=[CH:20][C:21]([O:24]C)=[CH:22][C:23]=4[C:15]=3[C:14]1=[O:29])[CH2:6]2.CO>ClCCl>[BrH:2].[N:5]12[CH2:12][CH2:11][CH:8]([CH2:9][CH2:10]1)[C@H:7]([N:13]1[CH:28]=[CH:27][C:16]3[N:17]([CH3:26])[C:18]4[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][C:23]=4[C:15]=3[C:14]1=[O:29])[CH2:6]2

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 15656893HCID 15656893, compound

Product 1

HCID 67877130HCID 67877130, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of BBr3 (0.5 mmol) in dichloromethane (0.5 ml) was added dropwise at -70° C. to a solution of (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-1,2-dihydro-8-methoxy-5-methyl-1-oxopyrido[4,3-b]indole (0.11 g, 0.33 mmol)in dichloromethane (1 ml), from Example 3. The reaction mixture was warmed to ambient temperature, then recooled to -70° C. Methanol (0.5 ml) was added and the reaction mixture was brought to ambient temperature. The solvent was removed under reduced pressure and the residue was recrystallized from isopropanol to afford 0.04 g (37% yield) of (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-1,2-dihydro-8-hydroxy-5-methyl-1-oxopyrido[4,3-b]indole hydrobromide, m.p. 235°-250° C.

Workup

  1. customrecooled to -70° C
  2. customwas brought to ambient temperature
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-d9324b867a6045ac92fbe5532f8396c7
Source dataset
uspto-grants-1993_02
Patent number
US05189041

Reaction notes

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