Boron tribromide → 1-(4-Benzo[b]thiophen-2-yl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-6,7-diol hydrobromide

HRID 2238356Notes

Reaction equation

HRID 2238356 reaction equation
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[C:11](C)[C:12]([O:20]C)=[C:13]([O:18]C)[CH:14]=2)[CH:9]1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[S:34][C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[CH:31]=2)=[CH:26][CH:25]=1)=O)(C)(C)C.B(Br)(Br)[Br:40]>ClCCl>[BrH:40].[S:34]1[C:30]([C:27]2[CH:28]=[CH:29][C:24]([CH2:23][CH:9]3[C:10]4[C:15](=[CH:14][C:13]([OH:18])=[C:12]([OH:20])[CH:11]=4)[CH2:16][CH2:17][NH:8]3)=[CH:25][CH:26]=2)=[CH:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]1=2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 865909591-(4-benzo[b]thiophen-2-yl-benzyl)-6,7-dimethoxy-8-methyl-3,4-dihydro-1-H-isoquinoline-2-carboxylic acid tert-butyl ester

Product 1

HCID 686841711-(4-Benzo[b]thiophen-2-yl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-6,7-diol hydrobromide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Benzo[b]thiophen-2-yl-benzyl)-1,2,3,4-tetrahydro-isoquinoline-6,7-diol hydrobromide (22) was prepared as follows: To a stirred solution of 0.15 g (0.29 mmole) of 1-(4-benzo[b]thiophen-2-yl-benzyl)-6,7-dimethoxy-8-methyl-3,4-dihydro-1-H-isoquinoline-2-carboxylic acid tert-butyl ester in 10 ml of anhydrous dichloromethane under argon at −70° C., 0.9 ml (3 mol. equiv.) of 1M boron tribromide solution in n-hexanes was added. The stirred mixture was allowed to reach room temperature overnight and 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, 130 mg (91%), mp 251-254° C.

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in 10 ml of methanol
  3. customagain, the solvent was evaporated under reduced pressure
  4. additionThe solid residue was mixed with 10 ml of ether
  5. customseparated on a glass
  6. filtrationfilter funnel
  7. washwashed with ether (3×20 ml)
  8. customto afford an off-white solid, 130 mg (91%), mp 251-254° C.

Sources & evidence

ORD record
ord-bc7ef6997a1743d8a646e724a6d26639
Source dataset
uspto-grants-2010_05
Patent number
US07718672B2

Reaction notes

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