Hydrochloric Acid → HCID 86593240, compound

HRID 1610361Notes

Reaction equation

HRID 1610361 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7].Cl.[CH2:27](OCC)[CH3:28]>[Cl-].[Zn+2].[Cl-]>[OH:3][CH:4]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=1)[C:6]([O:8][CH2:27][CH3:28])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 4311764Sodium borohydrideHCID 22262258HCID 22262258, compound

Product 1

HCID 86593240HCID 86593240, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

To a solution of zinc chloride (14.7 g, 108 mmol) in diethyl ether (250 ml) was added sodium borohydride (8.2 g, 216 mmol) and the mixture was stirred at room temperature for 2 hrs. The insoluble material was filtered off. To the filtrate was added a solution of 3-oxo-3-phenyl-2-((4-(trifluoromethyl)phenyl)methyl)propionic acid (22 g, 54 mmol) in diethyl ether (50 ml) and the mixture was stirred at room temperature for 30 min. 1N Hydrochloric acid was added to the reaction solution under ice-cooling for quenching, water (200 ml) was added, and 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 silica gel column chromatography (toluene) to give ethyl (2RS,3RS)-3-hydroxy-3-phenyl-2-((4-(trifluoromethyl)phenyl)methyl)propionate (15.6 g, 83%) 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. customfor quenching
  5. additionwater (200 ml) was added
  6. extractionthe mixture was extracted with ethyl acetate (300 ml×2)
  7. washThe extract was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (toluene)

Sources & evidence

ORD record
ord-0bbf0ca3c26a46c08582d4b01cb8b57d
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…