Hydrogen Bromide → HCID 19884868, compound

HRID 846176Notes

Reaction equation

HRID 846176 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][C:36]=1[O:37]C)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30]C)=[C:26]([O:32]C)[CH:25]=1.[BrH:39]>>[BrH:39].[BrH:39].[OH:32][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=1[OH:30])[CH2:23][CH:19]1[CH2:20][CH2:21][CH2:22][N:18]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][CH:7]1[CH2:6][C:5]1[CH:34]=[CH:35][C:36]([OH:37])=[C:3]([OH:2])[CH:4]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 19884871HCID 19884871, compound

Product 1

HCID 19884868HCID 19884868, compound

Procedure

A solution of 1,6-bis[2-(3,4-dimethoxybenzyl)pyrrolidin-1-yl]hexane (2.2 g, 4.4 mmol), from Step 2, was heated in 48% hydrobromic acid (11 mL) at reflux temperature for 3 hours (the reaction was followed by TLC on silica gel). The solution was cooled to room temperature; and the aqueous phase was decanted from the oil, which separated from solution. Toluene was added to this oil and then removed in vacuo. This addition and removal of toluene was repeated several times to remove water and hydrogen bromide. The residual solid, 1,6-bis[2-(3,4-dihydroxybenzyl)pyrrolidin-1-yl]hexane dihydrobromide, a mixture of the R,R-; S,S-; and R,S-stereoisomers, was obtained as a foam.

Workup

  1. temperatureat reflux temperature for 3 hours (the reaction
  2. customand the aqueous phase was decanted from the oil, which
  3. customseparated from solution
  4. additionToluene was added to this oil
  5. customremoved in vacuo
  6. additionThis addition and removal of toluene
  7. customto remove water and hydrogen bromide
  8. additionThe residual solid, 1,6-bis[2-(3,4-dihydroxybenzyl)pyrrolidin-1-yl]hexane dihydrobromide, a mixture of the R,R-
  9. customand R,S-stereoisomers, was obtained as a foam

Sources & evidence

ORD record
ord-d83ce3495a2d4896bbedb4713ae0ef22
Source dataset
uspto-grants-1992_08
Patent number
US05135944

Reaction notes

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