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

HRID 16322Notes

Reaction equation

HRID 16322 reaction equation
[F:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:9]/[CH3:10])[CH:5]=[C:4]([F:11])[C:3]=1[F:12].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:34]C)C=C4)N(CC2)C1.CS(N)(=O)=O.S([O-])([O-])=O.[Na+].[Na+].[OH2:82]>C(O)(C)(C)C>[F:1][C:2]1[CH:7]=[C:6]([C@H:8]([OH:34])[C@@H:9]([OH:82])[CH3:10])[CH:5]=[C:4]([F:11])[C:3]=1[F:12]

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

1,2,3-Trifluoro-5-((E)-propenyl)benzene (5.83 g) was added to a solution mixture of tert-butanol (170 mL) and water (170 mL) of AD-Mix-α (47.5 g) and methanesulfonamide (3.22 g) under ice-cooling. This reaction solution was stirred at 5° C. overnight. Then, sodium sulfite (51 g) was added to the reaction solution, and the resulting mixture was stirred at room temperature for 1 hr. The reaction solution was extracted with methylene chloride three times. All 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. All the organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue 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. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature for 1 hr
  3. extractionThe reaction solution was extracted with methylene chloride three times
  4. washwashed with a 2 N sodium hydroxide aqueous solution
  5. extractionThe sodium hydroxide layer was re-extracted with methylene chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1)

Sources & evidence

ORD record
ord-8b8e2cf6f40b47a49216c66ec44961da
Source dataset
uspto-grants-2010_06
Patent number
US07737141B2

Reaction notes

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