Methyl iodide → 1-(tert-Butyl) 2-methyl (2S,4S)-4-phenylpyrrolidine-1,2-dicarboxylate

HRID 238986Notes

Reaction equation

HRID 238986 reaction equation
[C:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][C@H:9]1[C:19]([OH:21])=[O:20])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:22](=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>CN(C)C=O>[CH3:22][O:20][C:19]([C@@H:9]1[CH2:10][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:12][N:8]1[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])=[O:21]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27559781-(1,1-Dimethylethyl) (2S,4S)-4-phenyl-1,2-pyrrolidinedicarboxylate

Product 1

HCID 580029141-(tert-Butyl) 2-methyl (2S,4S)-4-phenylpyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.48 g of commercially available (2S,4S)-Boc-4-phenyl-pyrrolidine-2-carboxylic acid (15.37 mmol) were dissolved in 50 ml dimethylformamide. 2.59 g of potassium carbonate (18.76 mmol) and 2.66 g of methyl iodide (18.76 mmol) were added and the reaction was stirred for 48 h at room temperature. Standard work-up with ethyl acetate yielded 5.3 of the product.

Sources & evidence

ORD record
ord-2f492d0283a34cdeb60ddc7e892a1b07
Source dataset
uspto-grants-2014_02
Patent number
US08642642B2

Reaction notes

Loading…