Hydrochloric Acid → ethyl (2RS,3RS)-3-[4-(methylsulfonyl)phenyl]-3-hydroxy-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate

HRID 1610677Notes

Reaction equation

HRID 1610677 reaction equation
[BH4-].[Na+].[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:34])[CH:14]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:33])([F:32])[CH:29]([F:31])[F:30])[CH:22]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=1)(=[O:6])=[O:5].Cl>C(OCC)C>[CH3:3][S:4]([C:7]1[CH:12]=[CH:11][C:10]([CH:13]([OH:34])[CH:14]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:32])([F:33])[CH:29]([F:30])[F:31])[CH:22]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=1)(=[O:5])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22261739Ethyl 3-[4-(methylsulfonyl)phenyl]-3-oxo-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate

Product 1

HCID 86593291ethyl (2RS,3RS)-3-[4-(methylsulfonyl)phenyl]-3-hydroxy-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of zinc chloride anhydride (1.72 g, 12.6 mmol) in diethyl ether (20 ml) was added sodium borohydride (0.95 g, 25.2 mmol) by small portions, and the mixture was stirred for 1 hr. Insoluble material was removed by filtration, and washed with diethyl ether. The filtrate was ice-cooled, and a solution of ethyl 3-[4-(methylsulfonyl)phenyl]-3-oxo-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate (3.0 g, 6.30 mmol) in diethyl ether (10 ml) was added. The mixture was stirred at room temperature for 1 hr. After ice-cooling again, 1N hydrochloric acid was added to terminate the reaction. The obtained mixture was extracted with ethyl acetate (100 ml), washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1-1:1) to give the objective substance (2.60 g, 86%) as a colorless oil.

Workup

  1. customInsoluble material was removed by filtration
  2. washwashed with diethyl ether
  3. temperaturecooled
  4. stirringThe mixture was stirred at room temperature for 1 hr
  5. temperatureAfter ice-cooling again
  6. customto terminate
  7. customthe reaction
  8. extractionThe obtained mixture was extracted with ethyl acetate (100 ml)
  9. washwashed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated under reduced pressure
  12. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1-1:1)
  13. customto give the objective substance (2.60 g, 86%) as a colorless oil

Sources & evidence

ORD record
ord-dc9eb58ec3484ce6af6255ae4e8e2b68
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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