Hydrochloric Acid → ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-[3-(isopropyloxy)benzyl]propanoate

HRID 1610644Notes

Reaction equation

HRID 1610644 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:28])[CH:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH:25]([CH3:27])[CH3:26])[CH:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.Cl>C(OCC)C.[Cl-].[Zn+2].[Cl-]>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([OH:28])[CH:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH:25]([CH3:27])[CH3:26])[CH:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22262205Ethyl 3-(4-fluorophenyl)-3-oxo-2-[3-(isopropyloxy)benzyl]propanoate

Product 1

HCID 86593286ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-[3-(isopropyloxy)benzyl]propanoate

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of anhydrous zinc chloride (9.12 g, 67.0 mmol) in diethyl ether (100 ml) was added sodium borohydride (5.07 g, 134 mmol) by small portions, and the mixture was stirred for 2 hrs. Insoluble material was filtered off, and washed with diethyl ether. The filtrate was ice-cooled, and to the filtrate was added a solution of ethyl 3-(4-fluorophenyl)-3-oxo-2-[3-(isopropyloxy)benzyl]propanoate (12.0 g, 33.5 mmol) in diethyl ether (20 ml). The mixture was stirred at room temperature for 2 hrs. and ice-cooled again. 1N Hydrochloric acid was added to stop the reaction. The mixture was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography(hexane:ethyl acetate=10:1) to give the objective substance (10 g, 83%) as a colorless oil

Workup

  1. filtrationInsoluble material was filtered off
  2. washwashed with diethyl ether
  3. temperaturecooled
  4. stirringThe mixture was stirred at room temperature for 2 hrs
  5. temperatureand ice-cooled again
  6. customthe reaction
  7. washThe mixture was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated under reduced pressure
  10. customThe residue was purified by silica gel chromatography(hexane:ethyl acetate=10:1)
  11. customto give the objective substance (10 g, 83%) as a colorless oil

Sources & evidence

ORD record
ord-1cba63e3550149b583f590d0fee172e3
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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