Hydrochloric Acid → HCID 22261661, compound

HRID 1610438Notes

Reaction equation

HRID 1610438 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:9]=[CH:8][C:7]([C:10](=[O:28])[CH:11]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][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-]>[Cl:3][C:4]1[N:9]=[CH:8][C:7]([CH:10]([OH:28])[CH:11]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:23]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22262302HCID 22262302, compound

Product 1

HCID 22261661HCID 22261661, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of zinc chloride (9.89 g, 72.6 mmol) in diethyl ether (150 ml) was added sodium borohydride (5.49 g, 145 mmol), and the mixture was stirred at room temperature for 30 min. The insoluble material was filtered off, and a solution of ethyl 3-(6-chloro-3-pyridyl)-3-oxo-2-((4-(trifluoromethyl)phenyl)methyl)propionate (14 g, 36.3 mmol) in diethyl ether (50 ml) was added to the filtrate. The mixture was stirred at room temperature for 30 min. 1N Hydrochloric acid was added to the reaction solution under ice-cooling to quench the reaction and water (200 ml) was added. The mixture was extracted with ethyl acetate (300 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by medium pressure silica gel column chromatography (hexane:ethyl acetate=4:1) to give ethyl(2RS,3RS)-3-(6-chloro-3-pyridyl)-3-hydroxy-2-((4-(trifluoromethyl)phenyl)methyl)propionate (9.32 g, 66%) as a colorless oil.

Workup

  1. filtrationThe insoluble material was filtered off
  2. stirringThe mixture was stirred at room temperature for 30 min
  3. temperaturecooling
  4. customto quench
  5. customthe reaction and water (200 ml)
  6. additionwas added
  7. extractionThe mixture was extracted with ethyl acetate (300 ml×2)
  8. washThe extract was washed with water and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated under reduced pressure
  11. customThe residue was purified by medium pressure silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-6add1d1c7cdf47b38b37e796a3c86890
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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