Dimethyl Sulfoxide → (3S)-3-Formyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester

HRID 1917358Notes

Reaction equation

HRID 1917358 reaction equation
[C:1]([O:5][C:6]([C@@:8]1([CH2:22][OH:23])[CH2:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(C)=O>ClCCl>[C:1]([O:5][C:6]([C@@:8]1([CH:22]=[O:23])[CH2:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 57758657HCID 57758657, compound

Product 1

HCID 86664650(3S)-3-Formyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl esterYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S)-3-Hydroxymethyl-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylic acid tert-butyl ester (4.0 g, 12.52 mmol) was dissolved in dichloromethane. Triethylamine (6.34 g, 62.62 mmol), dimethyl sulfoxide (3.91 g, 50.09 mmol), and a SO3-pyridine complex (3.99 g, 25.05 mmol) were sequentially added at 0° C., and the mixture was stirred for 17 hours. The reaction solution was concentrated under reduced pressure, and water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (60% ethyl acetate/hexane) to give 2.85 g of the title compound as a colorless solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-8c1b0496ce684e3f98bd63c1da025d78
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

Loading…