Water → 2-Benzyl-6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 2390038Notes

Reaction equation

HRID 2390038 reaction equation
[CH2:1]([N:8]1[CH:17]([C:18]([O:20]C)=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:22])[CH:14]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].O.[Cl-].[NH4+]>C1COCC1>[CH2:1]([N:8]1[CH:17]([C:18]([OH:20])=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([F:22])[CH:14]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 3939Lithium HydroxideHCID 25517Ammonium ChlorideHCID 59323112Methyl 2-benzyl-6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

Product 1

HCID 593233962-Benzyl-6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

460 mg of methyl 2-benzyl-6-fluoro-1,2,3,4-tetrahydroisoquinoline-3-carboxylate and 640 mg of lithium hydroxide.monohydrate were dissolved in 5 mL of THF:H2O=1:1, followed by stirring under reflux for 1 hour. Water was added to the reaction liquid, followed by neutralization by addition of ammonium chloride and an aqueous sodium bicarbonate solution and extraction with chloroform, and the organic layer was then washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 436 mg (yield 99%) of a title compound as a pale yellow oily substance.

Workup

  1. temperatureunder reflux for 1 hour
  2. extractionan aqueous sodium bicarbonate solution and extraction with chloroform
  3. washthe organic layer was then washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8f19ca710ee24bdb8a86b2b2f70b1525
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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