Water → 2-phenyl-3-methyl-8-(1-(S),2-dihydroxyethyl)quinoline

HRID 1167180Notes

Reaction equation

HRID 1167180 reaction equation
[C:1]1([C:7]2[C:16]([CH3:17])=[CH:15][C:14]3[C:9](=[C:10]([CH:18]=[CH2:19])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:41]C)C=C4)N(CC2)C1.[O-]S([O-])=O.[Na+].[Na+].[OH2:84]>C(O)(C)(C)C>[C:1]1([C:7]2[C:16]([CH3:17])=[CH:15][C:14]3[C:9](=[C:10]([C@H:18]([OH:41])[CH2:19][OH:84])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 24437Sodium SulfiteHCID 229959252-Phenyl-3-methyl-8-vinylquinolineHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine

Product 1

HCID 213565432-phenyl-3-methyl-8-(1-(S),2-dihydroxyethyl)quinolineYield 69%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

8.6 g (35 mmol) of 2-phenyl-3-methyl-8-vinylquinoline are added, at 0° C., to a suspension of 52 g of AD-mix-α in a mixture of 200 ml of distilled water and 200 ml of tert-butanol. The reaction mixture is then vigorously stirred for 16 hours at this same temperature using a mechanical stirrer. 2 g of Na2SO3 are then added. The reaction mixture is stirred for one hour and is then taken up in 200 ml of water and extracted with 3×200 ml of ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7) to provide 6.65 g of 2-phenyl-3-methyl-8-(1-(S),2-dihydroxyethyl)quinoline in the form of an orange-colored solid; M.p.=117° C. (Yield: 69%)

Workup

  1. stirringThe reaction mixture is stirred for one hour
  2. extractionextracted with 3×200 ml of ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7)

Sources & evidence

ORD record
ord-044536a0525e482f8781c0c0be39cff0
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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