Oxygen → HCID 69472649, compound

HRID 1374462Notes

Reaction equation

HRID 1374462 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][CH:11]=[CH:12][CH3:13])[CH2:7][N:6]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:4].[O:21]=O>CN(C=O)C.O.[Pd](Cl)Cl.[Cu]Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([CH2:10][CH2:11][C:12](=[O:21])[CH3:13])[CH2:7][N:6]1[C:14]([O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:15])=[O:4]

Participants

7

Reactant 2

HCID 977OxygenHCID 69470518HCID 69470518, compound

Product 1

HCID 69472649HCID 69472649, compoundYield 71%

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-but-2-enyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (149 mg, 0.42 mmol, 1 equiv) in DMF (1.4 mL) and water (0.2 mL) were added palladium(II)chloride (7.4 mg, 0.042 mmol, 0.1 equiv) and copper(I) chloride (41.1 mg, 0.42 mmol, 1 equiv). The mixture was stirred at 50° C. overnight with oxygen bubbling into the mixture. The mixture was filtered and the filtrate was concentrated under high vacuum. The residue was diluted with ethyl acetate, washed with water (1×), brine (1×), dried and concentrated. The residue was purified by preparative TLC to give 4-(3-oxo-butyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (110 mg, 71%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated under high vacuum
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water (1×), brine (1×)
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-f0446cfd105e4113943dcc653c939815
Source dataset
uspto-grants-2007_01
Patent number
US07164011B2

Reaction notes

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