Hydrochloric Acid → HCID 17862110, compound

HRID 1610717Notes

Reaction equation

HRID 1610717 reaction equation
[BH4-].[Na+].[C:3]([C:7]1[CH:28]=[CH:27][C:10]([CH2:11][CH:12]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].Cl>CCOCC.C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[C:3]([C:7]1[CH:28]=[CH:27][C:10]([CH2:11][CH:12]([CH:18]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[OH:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:5])[CH3:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22261735HCID 22261735, compound

Product 1

HCID 17862110HCID 17862110, compoundYield 92.4%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension (80 ml) of zinc chloride (6.59 g, 48.3 mol) in ether was added sodium borohydride (3.66 g, 96.6 mol) at room temperature and the mixture was stirred as it as for 2 hrs. A solution of ethyl 2-[4-(tert-butyl)benzyl]-3-(4-fluorophenyl)-3-oxopropionate (8.61 g, 24.15 mmol) in ether (40 ml) was added, and the mixture was stirred at room temperature for 15 min. The reaction was stopped with 1N hydrochloric acid, and the reaction solution was diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1, 5:1) to give ethyl (2RS,3RS)-2-[4-(tert-butyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionate (8.00 g, 92%) as a colorless transparent oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 min
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1, 5:1)

Sources & evidence

ORD record
ord-52a6beb3965643be8735db9d4a220ceb
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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