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

HRID 880661Notes

Reaction equation

HRID 880661 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 (1 M, 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-d7a3bd941ae3414cac12af074b7733ac
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Reaction notes

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