Water → HCID 54443561, compound

HRID 1872757Notes

Reaction equation

HRID 1872757 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[CH2:6].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:31]C)C=C4)N(CC2)C1.[O-]S([O-])=O.[Na+].[Na+].[OH2:74]>CC(O)(C)C>[CH3:1][C:2]1[CH:3]=[C:4]([C@H:5]([OH:31])[CH2:6][OH:74])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 75291-Ethenyl-3-methylbenzeneHCID 24437Sodium SulfiteHCID 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 54443561HCID 54443561, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-methylstyrene (1.69 ml, 12.7 mmol), and AD-mix-α (17.78 g, 12.7 mmol) in water (65 ml) and t-BuOH (65 ml) was stirred at 0° C. for 3.5 h. To this reaction mixture was added Na2SO3 (20 g) and the mixture was stirred at rt for 1 h. The reaction mixture was extracted with ethyl acetate. The extract was washed with brine, dried (Na2SO4), and concentrated to give 2.07 g of light brown oil, which was purified by column chromatography (silica gel: 110 g, ethyl acetate/hexane: 3/2) to afford 1.89 g (98%) of desired product as light brown oil.

Workup

  1. stirringthe mixture was stirred at rt for 1 h
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-440b35928172412c9286c80fd1c81775
Source dataset
uspto-grants-2000_08
Patent number
US06110947

Reaction notes

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