Acetic Acid → HCID 23160691, compound

HRID 1360391Notes

Reaction equation

HRID 1360391 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7][CH:6]2[OH:13].[C:16](O)(=O)[CH3:17].[C:20](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:20]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:12][CH:11]=2)[CH:6]([OH:13])[CH2:7][CH2:8]1)[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 23160669HCID 23160669, compound

Product 1

HCID 23160691HCID 23160691, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-(Trifluoromethyl)-1,2,3,4-tetrahydroquinolin-4-ol (30 mg, 0.14 mmol) obtained in Step 2 was dissolved in methylene chloride (2 ml), propylaldehyde (16 mg, 0.28 mmol), acetic acid (20 μl) and sodium triacetoxyborohydride (59 mg, 0.28 mmol) were added, and the mixture was stirred overnight. The solvent was evaporated, and the residue was subjected to reversed-phase high performance liquid chromatography using ODS as a filler, and eluted with a mixed solution of water and acetonitrile, which contains 0.1% (v/v) trifluoroacetic acid. Aqueous sodium hydrogencarbonate solution was added to the object fraction. Acetonitrile was evaporated under reduced pressure and the remaining aqueous layer was partitioned with ethyl acetate. The solvent was evaporated to dryness to give the title compound (10.4 mg, 0.04 mmol, 29%).

Workup

  1. customThe solvent was evaporated
  2. washeluted with a mixed solution of water and acetonitrile, which
  3. additionAqueous sodium hydrogencarbonate solution was added to the object fraction
  4. customAcetonitrile was evaporated under reduced pressure
  5. customthe remaining aqueous layer was partitioned with ethyl acetate
  6. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-69fa6dd255224272bcae7ee2ba1e5c8e
Source dataset
uspto-grants-2011_02
Patent number
US07879863B2

Reaction notes

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