Methanol → HCID 19884867, compound

HRID 846175Notes

Reaction equation

HRID 846175 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.B(Br)(Br)Br.CO>C(Cl)Cl>[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

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 19884871HCID 19884871, compound

Product 1

HCID 19884867HCID 19884867, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

1,6-bis[2-(3,4-dimethoxybenzyl)pyrrolidin-1-yl]hexane was dissolved in dry CH2Cl2 and cooled to -70° C. under inert atmosphere. BBr3 was added. The mixture was warmed to room temperature and CH3OH was added. The solvent was removed in vacuo to give 1,6-bis-[2-(3,4-dihydroxybenzyl)pyrrolidin-1-yl]hexane.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cf24988ea24340b1977c3126e46b4622
Source dataset
uspto-grants-1992_08
Patent number
US05135944

Reaction notes

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