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

HRID 1610545Notes

Reaction equation

HRID 1610545 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:38])[CH:18]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]([F:37])([F:36])[CH:33]([F:35])[F:34])[CH:26]=2)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.O>C(OCC)C.[Cl-].[Zn+2].[Cl-]>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([OH:38])[CH:18]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]([F:36])([F:37])[CH:33]([F:34])[F:35])[CH:26]=2)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 22261555Ethyl 3-[4-(benzyloxy)phenyl]-3-oxo-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate

Product 1

HCID 22261603ethyl(2RS,3RS)-3-[4-(benzyloxy)phenyl]-3-hydroxy-2-[3-(1,1,2,2-tetrafluoroethoxy) benzyl]propanoate

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of zinc chloride (18.9 g, 139 mmol) in diethyl ether (500 ml) was added sodium borohydride (10.5 g, 278 mmol), and the mixture was stirred at room temperature for 30 min. Insoluble material was filtered off. To the filtrate was added a solution of ethyl 3-[4-(benzyloxy)phenyl]-3-oxo-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate (35.0 g, 69.4 mmol) in diethyl ether (200 ml) at 0° C., and the mixture was stirred for 30 min. 1N Hydrochloric acid was added to the reaction solution to stop the reaction. Then, water (500 ml) was added and the mixture was extracted with ethyl acetate (500 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) and recrystallized from ethyl acetate-hexane to give the objective substance (30.3 g, 86%).

Workup

  1. filtrationInsoluble material was filtered off
  2. stirringthe mixture was stirred for 30 min
  3. customthe reaction
  4. extractionthe mixture was extracted with ethyl acetate (500 ml×2)
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)
  9. customrecrystallized from ethyl acetate-hexane
  10. customto give the objective substance (30.3 g, 86%)

Sources & evidence

ORD record
ord-b373f3d4b3b64d1988284e94ef781226
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…