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

HRID 1436106Notes

Reaction equation

HRID 1436106 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 an ice-cooled mixed solution of AD-Mix-α (47.5 g) and methanesulfonamide (3.22 g) in tert-butanol (170 ml) and water (170 ml), and the reaction solution was stirred at 5° C. overnight. Then, sodium sulfite (51 g) was added to the reaction solution, which was then stirred for one hour. The reaction solution was subjected to extraction with methylene chloride three times. The combined organic layers were washed with a 2 N sodium hydroxide solution, and then the sodium hydroxide layer was subjected to extraction with methylene chloride again. The organic layers were combined and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1) to obtain 5.54 g of the title compound.

Workup

  1. temperaturecooled
  2. stirringwas then stirred for one hour
  3. extractionThe reaction solution was subjected to extraction with methylene chloride three times
  4. washThe combined organic layers were washed with a 2 N sodium hydroxide solution
  5. extractionthe sodium hydroxide layer was subjected to extraction with methylene chloride again
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to 1:1)

Sources & evidence

ORD record
ord-3875aac87df74fa89a28e5bfc52c2aa0
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

Loading…