Water → (1S,2S)-1-(3,4,5-trifluorophenyl)propane-1,2-diol

HRID 16354Notes

Reaction equation

HRID 16354 reaction equation
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:22]C)C=C4)N(CC2)C1.CS(N)(=O)=O.[F:64][C:65]1[CH:70]=[C:69](/[CH:71]=[CH:72]/[CH3:73])[CH:68]=[C:67]([F:74])[C:66]=1[F:75].S([O-])([O-])=O.[Na+].[Na+].[OH2:82]>C(O)(C)(C)C>[F:64][C:65]1[CH:70]=[C:69]([C@H:71]([OH:22])[C@@H:72]([OH:82])[CH3:73])[CH:68]=[C:67]([F:74])[C:66]=1[F:75]

Participants

7

Reactant 5

HCID 962WaterHCID 24437Sodium SulfiteHCID 72879MethanesulfonamideHCID 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)phthalazineHCID 687165151,2,3-trifluoro-5-((E)-propenyl)benzene

Product 1

HCID 68718224(1S,2S)-1-(3,4,5-trifluorophenyl)propane-1,2-diol

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
5 °C

Procedure

To an ice-cooled solution mixture of tert-butanol (170 mL) and water (170 mL) of AD-Mix-α (47.5 g) and methanesulfonamide (3.22 g), 1,2,3-trifluoro-5-((E)-propenyl)benzene (5.83 g) was added. The resulting reaction solution was stirred at 5° C. overnight, and then sodium sulfite (51 g) was added thereto. The resulting reaction solution was stirred at room temperature for 1 hr, and then extracted with methylene chloride three times. The organic layers were combined and washed with a 2 N sodium hydroxide aqueous solution. The sodium hydroxide layer was re-extracted with methylene chloride. The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1) to give 5.54 g of the title compound. The physical property values of this compound were as follows:

Workup

  1. additionwas added
  2. customThe resulting reaction solution
  3. customThe resulting reaction solution
  4. stirringwas stirred at room temperature for 1 hr
  5. extractionextracted with methylene chloride three times
  6. washwashed with a 2 N sodium hydroxide aqueous solution
  7. extractionThe sodium hydroxide layer was re-extracted with methylene chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe obtained crude product
  11. customwas purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1)

Sources & evidence

ORD record
ord-0058a6d75809434ea5039ede7fa50892
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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