Boron tribromide → 1-[1,1';4',1'']Terphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol hydrobromide

HRID 2238354Notes

Reaction equation

HRID 2238354 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:20]C)=[C:13]([O:18]C)[CH:14]=2)[CH:9]1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)=[CH:25][CH:24]=1)=O)(C)(C)C.B(Br)(Br)[Br:42]>ClCCl>[BrH:42].[C:26]1([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:31][CH:30]=2)[CH:27]=[CH:28][C:23]([CH2:22][CH:9]2[C:10]3[C:15](=[CH:14][C:13]([OH:18])=[C:12]([OH:20])[CH:11]=3)[CH2:16][CH2:17][NH:8]2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 589064756,7-Dimethoxy-1-[1,1';4',1'']terphenyl-4-ylmethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 686858311-[1,1';4',1'']Terphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol hydrobromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[1,1′;4′,1″]Terphenyl-4-ylmethyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol hydrobromide (13) was prepared as follows: To a stirred solution of 0.10 g (0.187 mmol) of 6,7-dimethoxy-1-[1,1′;4′,1″]terphenyl-4-ylmethyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester in 10 ml of anhydrous dichloromethane under argon at −70° C., 1 ml (5 mol. equiv.) of 1M boron tribromide solution in n-hexanes was added. The mixture was allowed to reach room temperature with stirring overnight and then the solvents were evaporated under reduced pressure. The residue was dissolved in 10 ml of methanol and, again, the solvent was evaporated under reduced pressure. The solid residue was mixed with 10 ml of ether, separated on a glass filter funnel, washed with ether (3×20 ml) to afford an off-white solid, 82 mg (90%), mp 262-264° C.

Workup

  1. customto reach room temperature
  2. customthe solvents were evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in 10 ml of methanol
  4. customagain, the solvent was evaporated under reduced pressure
  5. additionThe solid residue was mixed with 10 ml of ether
  6. customseparated on a glass
  7. filtrationfilter funnel
  8. washwashed with ether (3×20 ml)
  9. customto afford an off-white solid, 82 mg (90%), mp 262-264° C.

Sources & evidence

ORD record
ord-194a75bf891a466ab77c81834bf59603
Source dataset
uspto-grants-2010_05
Patent number
US07718672B2

Reaction notes

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