Ammonium Chloride → HCID 22448946, compound

HRID 2186742Notes

Reaction equation

HRID 2186742 reaction equation
[C:1]1([C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([S:9][CH2:10][C:11]([N:13]2[C:22]3[C:17](=[C:18]([OH:23])[CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=O)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B.C1COCC1.[Cl-].[NH4+]>C1COCC1>[C:24]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([S:9][CH2:10][CH2:11][N:13]2[C:22]3[C:17](=[C:18]([OH:23])[CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][CH2:14]2)[CH3:8])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2723981Borane;tetrahydrofuranHCID 22448980HCID 22448980, compound

Product 1

HCID 22448946HCID 22448946, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-((1,1-diphenylethylthio)acetyl)-5-hydroxy-1,2,3,4-tetrahydroquinoline (136 mg) was dissolved in THF (5 ml), and the resultant solution was stirred at 0° C. A borane THF complex (1.0N in THF) (2.0 ml) was added to the solution, and the mixture was stirred at room temperature. After disappearance of the raw materials was confirmed, the reaction solution was added to a saturated ammonium chloride aqueous solution (20 ml), and then extracted with ethyl acetate. The resultant organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and a concentrated. The resultant residue was purified by column chromatography (silica gel:hexane/ethyl acetate=5/1) to obtain the object compound (60 mg, yield 46%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe resultant organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe resultant residue was purified by column chromatography (silica gel:hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-e980f6492db842579779b421d46f7fd9
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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