Ammonium Chloride → HCID 58860038, compound

HRID 1785920Notes

Reaction equation

HRID 1785920 reaction equation
[C:1]([C:4]1[CH:33]=[CH:32][C:7]([C:8]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C@H:13]([N:20]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:21](=[O:23])[CH3:22])[CH2:12][C@@H:11]2[CH3:31])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:34][Mg]Br.[Cl-].[NH4+]>C1COCC1>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([N:20]([C@H:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:10]([C:8](=[O:9])[C:7]3[CH:32]=[CH:33][C:4]([C:1]([OH:3])([CH3:34])[CH3:2])=[CH:5][CH:6]=3)[C@@H:11]([CH3:31])[CH2:12]2)[C:21](=[O:23])[CH3:22])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 68924145HCID 68924145, compound2×HCID 178418573HCID 178418573, compound

Product 1

HCID 58860038HCID 58860038, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(2S,4R)-N-(4-Chloro-phenyl)-N-{1-[4-(1-hydroxy-1-methyl-ethyl)-benzoyl]-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl}-acetamide was prepared from (2S,4R)-N-[1-(4-acetyl-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-(4-chloro-phenyl)-acetamide. (2S,4R)-N-[1-(4-Acetyl-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-N-(4-chloro-phenyl)-acetamide (112 mg, 124 mmol) was dissolved in THF (5 mL) and cooled to 0° C. Methyl magnesium bromide (1.4 M in ether, 2 mL, 2.4 mmol) was added and the mixture stirred at 0° C. for 2 h. The reaction was warmed to rt and stirred an additional 2 h. The reaction was poured into saturated aqueous ammonium chloride. The phases were separated and the aqueous was extracted with ethyl acetate. The extracts were washed with brine, dried over magnesium sulfate, filtered, dried and concentrated. The crude alcohol was purified by silica gel chromatography to afford pure product (20 mg, 24%).

Workup

  1. temperatureThe reaction was warmed to rt
  2. stirringstirred an additional 2 h
  3. customThe phases were separated
  4. extractionthe aqueous was extracted with ethyl acetate
  5. washThe extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customdried
  9. concentrationconcentrated
  10. customThe crude alcohol was purified by silica gel chromatography

Sources & evidence

ORD record
ord-258b5262bc1b4c1995a55ec514facab1
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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