Boron tribromide → 6-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

HRID 1384962Notes

Reaction equation

HRID 1384962 reaction equation
Cl.C[O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[N:9](CCN1CCC(C3C=CC=CC=3)CC1)[CH2:8][CH2:7]2.B(Br)(Br)Br>C(Cl)Cl>[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[NH:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 131722774HCID 131722774, compound

Product 1

HCID 159083146-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-oneYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the title A compound of Example 1 (3.8 g, 21.5 mmol; 3,4-dihydro-6-methoxy-2-[2-(4-phenyl-1-piperidinyl)-ethyl]-1(2H)-isoquinolinone, monohydrochloride) in methylene chloride (50 mL) at −78° C. was added a solution of boron tribromide (1M, 53.7 mL, 53.7 mmol) under nitrogen. The reaction mixture was stirred at for 16 hours, quenched with saturated amminium chloride solution and extracted repeatedly with EtOAc. The organic layer was dried over MgSO4 and concentrated to give the crude product which was triturated with acetone to afford the title compound (2.3 g, 66% yield) as an off-white solid.

Workup

  1. customquenched with saturated amminium chloride solution
  2. extractionextracted repeatedly with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customwas triturated with acetone

Sources & evidence

ORD record
ord-0cc13f1a3f574636950150c042a8336f
Source dataset
uspto-grants-2001_07
Patent number
US06262068B1

Reaction notes

Loading…