Tetrahydrofuran → HCID 117839862, compound

HRID 1477665Notes

Reaction equation

HRID 1477665 reaction equation
O1CCCC1.Br[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.C([Li])CCC.[CH3:19][CH:20]1[CH2:25][C:24](=[O:26])[CH2:23][CH2:22][N:21]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>C(OCC)(=O)C.O>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C:24]2([OH:26])[CH2:23][CH2:22][N:21]([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH:20]([CH3:19])[CH2:25]2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 99931-Bromo-4-fluorobenzeneHCID 12992764tert-Butyl 2-methyl-4-oxopiperidine-1-carboxylateHCID 178418339Butyllithium

Product 1

HCID 117839862HCID 117839862, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (10 mL) of 1-bromo-4-fluorobenzene (492 mg, 2.81 mmol), n-butyl lithium (1.62 M, hexane solution) (1.73 mL, 2.81 mmol) was added at −78° C. and the resultant mixture was stirred for 40 minutes. To the reaction solution, a tetrahydrofuran solution of tert-butyl 2-methyl-4-oxopiperidine-1-carboxylate (500 mg, 2.34 mmol) was added and the resultant mixture was stirred at room temperature for 1 day. After completion of the reaction, water was added to the reaction solution and extraction from the resultant mixture with ethyl acetate was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product (729 mg) of the title compound.

Workup

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-421e59abf1644513879dabe0615ba48e
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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