Methanol → 3-(5-Fluoro-4-hydroxy-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline

HRID 1867233Notes

Reaction equation

HRID 1867233 reaction equation
[BH4-].[Na+].CO.[F:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8](=[O:28])[C:9]([CH3:27])([CH3:26])[N:10]=[C:11]2[C:16]1[CH:17]=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2>O>[F:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]([OH:28])[C:9]([CH3:26])([CH3:27])[N:10]=[C:11]2[C:16]1[CH:17]=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 231608453-(5-Fluoro-4-keto-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline

Product 1

HCID 231608883-(5-Fluoro-4-hydroxy-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolineYield 74.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium borohydride (103 mg) was added to a methanol (8 mL) solution of 3-(5-fluoro-4-keto-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (300 mg, 0.9 mmol) followed by stirring for 2.5 hours at room temperature, pouring water, extracting with ethyl acetate, and applying the resulting residue to chromatography to obtain 215 mg (yield 74%) of the target compound.

Workup

  1. extractionextracting with ethyl acetate

Sources & evidence

ORD record
ord-3557a81738e747a3b53b9fbb62f170a1
Source dataset
uspto-grants-2009_12
Patent number
US07632783B2

Reaction notes

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