Sodium borohydride → (3-(3,4-Dichlorophenyl)-5-oxopyrrolidin-3-yl)acetic acid ethyl ester

HRID 1682932Notes

Reaction equation

HRID 1682932 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]([C:21]#[N:22])([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)[CH2:7][C:8](OCC)=[O:9])[CH3:2].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Co](Cl)Cl>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][C:6]1([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=2)[CH2:7][C:8](=[O:9])[NH:22][CH2:21]1)[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 54083037Diethyl 3-cyano-3-(3,4-dichlorophenyl)pentanedioate

Product 1

HCID 54080079(3-(3,4-Dichlorophenyl)-5-oxopyrrolidin-3-yl)acetic acid ethyl esterYield 85.1%

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent

Procedure

3-Cyano-3-(3,4-dichloro-phenyl)-pentanedioic acid diethyl ester (10 g; 27.94 mmol) was dissolved in methanol (100 mL) and cobalt(II)chloride hexahydrate (13.2 g, 55.48 mmol) was added. The solution was then cautiously treated with one gram portions of sodium borohydride (11 g, 290 mmol) over 45 minutes at 20°-30° C. The solution was allowed to stir an additional 1.5 hours and the solution was concentrated in vacuo. The residue was partitioned between dichloromethane and 1N HCl the organic phase was and washed with 1N HCl (700 mL). The organic phase was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (600 g) with a gradient of 3% to 6% methanol in dichloromethane to give 7.514 g (85%) of the title compound.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customThe residue was partitioned between dichloromethane and 1N HCl the organic phase
  3. washwashed with 1N HCl (700 mL)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel (600 g) with a gradient of 3% to 6% methanol in dichloromethane

Sources & evidence

ORD record
ord-f8cb6542745a45bfb78829213575f8ee
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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