Methanol → 6-(3-Fluoro-benzyloxy)-2-(2-hydroxy-1-methyl-ethyl)-3,4-dihydro-2H-isoquinolin-1-one

HRID 2415439Notes

Reaction equation

HRID 2415439 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH:18]([CH3:22])[C:19](O)=[O:20])[CH2:11][CH2:10]2.CO>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[N:12]([CH:18]([CH3:22])[CH2:19][OH:20])[CH2:11][CH2:10]2

Participants

4

Reactant 2

HCID 887MethanolHCID 226419002-[6-(3-Fluoro-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-propionic Acid

Product 1

HCID 226419476-(3-Fluoro-benzyloxy)-2-(2-hydroxy-1-methyl-ethyl)-3,4-dihydro-2H-isoquinolin-1-oneYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 2-[6-(3-fluoro-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid (see example 3) (0.029 g, 0.058 mmol) was diluted in tetrahydrofuran (0.5 mL) and borane-methyl sulfide complex was added (0.017 mL, 0.175 mmol) at −20° C. The mixture was stirred 2 h from −20° C. to room temperature. Methanol was added and the solvents evaporated under vacuum. The resulting solid formed was purified by chromatography (SiO2, CH2Cl2/MeOH 9:1 v:v) to give the title compound as a white solid (0.018 g, 94%). MS: m/e=330.4 (M+H+).

Workup

  1. additionborane-methyl sulfide complex was added (0.017 mL, 0.175 mmol) at −20° C
  2. customthe solvents evaporated under vacuum
  3. customThe resulting solid formed
  4. customwas purified by chromatography (SiO2, CH2Cl2/MeOH 9:1 v:v)

Sources & evidence

ORD record
ord-6c01c578011441e9bfa86f3e5f833cc2
Source dataset
uspto-grants-2004_11
Patent number
US06818774B2

Reaction notes

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