Water → 6-Fluoro-1,2,3,4-tetrahydroisoquinoline

HRID 2067785Notes

Reaction equation

HRID 2067785 reaction equation
B#B.[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=O)[NH:9][CH2:8][CH2:7]2.O>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][NH:9][CH2:8][CH2:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 6328200DiboronHCID 107257096-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one

Product 1

HCID 157187246-Fluoro-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diborane (1M, THF, 24 mL) was added at 0° C. to a solution of 6-fluoro-3,4-dihydro isoquinolin-1(2H)-one (1.14 g, 6.9 mmol) in THF (8 mL). The mixture was stirred at reflux for 18 h. It was cooled to room temperature and water was added. The mixture was extracted with dichloromethane, and the organic layer was dried over sodium sulfate and concentrated. Purification by column chromatography (hexanes:ethyl acetate 1:1) afforded the title compound.

Workup

  1. temperatureat reflux for 18 h
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by column chromatography (hexanes:ethyl acetate 1:1)

Sources & evidence

ORD record
ord-ae0390d0012e49e7b31fb1302589b91f
Source dataset
uspto-grants-2012_10
Patent number
US08293911B2

Reaction notes

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