Acetic Acid → HCID 59166772, compound

HRID 1442970Notes

Reaction equation

HRID 1442970 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=O)[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][CH:25]=1)[NH2:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@H:8]([NH:22][C:21]2[CH:23]=[CH:24][CH:25]=[C:19]([Cl:18])[CH:20]=2)[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 79323-ChloroanilineHCID 42518531-tert-Butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 59166772HCID 59166772, compoundYield 40.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (364.5 mg, 1.5 mmol) and 3-chloroaniline (191 mg, 1.5 mmol) were dissolved in DCM (10 ml). To this solution was added sodium triacetoxyborohydride (413 mg, 1.95 mmol) and acetic acid (0.085 ml, 1.5 mmol), and the reaction stirred at room temperature overnight. The reaction mixture was washed with 2N NaOH (5 ml), saturated brine (5 ml), dried over MgSO4 and evaporated. The residue was purified by flash chromatography on silica eluting with DCM to give the title compound as a colourless oil (215 mg, 40%).

Workup

  1. washThe reaction mixture was washed with 2N NaOH (5 ml), saturated brine (5 ml)
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified by flash chromatography on silica eluting with DCM

Sources & evidence

ORD record
ord-bbb3cb0d846c470497aa145b7bd5ec20
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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