Hydrochloric Acid → ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(4-isopropylbenzyl)propionate

HRID 1610299Notes

Reaction equation

HRID 1610299 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.Cl>C(OCC)C.[BH4-].[Zn+2].[BH4-]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:25])[CH:9]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:20][CH:21]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22261387Ethyl 3-(4-fluorophenyl)-2-(4-isopropylbenzyl)-3-oxopropionate

Product 1

HCID 86593227ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-(4-isopropylbenzyl)propionate

Reagents, catalysts & solvents 2

HCID 12838295ZINC;boranuideCatalystHCID 3283Diethyl EtherSolvent

Procedure

While stirring zinc chloride (8.41 g, 61.7 mmol) in diethyl ether (100 ml), sodium borohydride (4.67 g, 123 mmol) was added at room temperature and the mixture was stirred as it was for 2 hrs. The insoluble material of the mixture was removed by filtration and washed with diethyl ether to give a solution of zinc borohydride in diethyl ether. To the obtained solution was added a solution of ethyl 3-(4-fluorophenyl)-2-(4-isopropylbenzyl)-3-oxopropionate (10.57 g, 30.87 mmol) in diethyl ether (50 ml) at room temperature and the mixture was stirred as it was for 2 hrs. Dilute hydrochloric acid was added to the reaction solution by small portions to decompose excess zinc borohydride. The mixture was extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1) to give the objective substance.

Workup

  1. extractionThe mixture was extracted twice with ethyl acetate
  2. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-6906d07889f341beb59f0d33bacfd7fd
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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