Dimethyl Sulfoxide → 2-Boc-5-oxo-octahydro-isoindole

HRID 1059314Notes

Reaction equation

HRID 1059314 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:26][CH:25]2[CH:20]([CH2:21][CH2:22][CH:23]([OH:27])[CH2:24]2)[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16]([N:18]1[CH2:26][CH:25]2[CH:20]([CH2:21][CH2:22][C:23](=[O:27])[CH2:24]2)[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 186703241,1-Dimethylethyl octahydro-5-hydroxy-2H-isoindole-2-carboxylate

Product 1

HCID 186704572-Boc-5-oxo-octahydro-isoindoleYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-78 °C

Procedure

4.9 g of oxalyl chloride was dissolved in 250 ml of dichloromethane and cooled to −78° C. in a nitrogen atmosphere. Then a solution of 4.83 g of dimethyl sulfoxide in dichloromethane (20 ml) was dropped thereinto over 17 minutes. Subsequently, a solution of 3.73 g of 8-(tert-butoxycarbonyl)-8-azabicyclo[4.3.0]nonan-3-ol in dichloromethane (40 ml) was dropped thereinto over 10 minutes. After stirring for 10 minutes, 7.82 g of triethylamine was dropped thereinto over 10 minutes and stirring was continued for additional 1 hour. The reaction mixture was brought back to room temperature, diluted with dichloromethane, washed with water and a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 3.21 g of the title compound as a colorless oily substance.

Workup

  1. waitover 10 minutes
  2. waitover 10 minutes
  3. stirringstirring
  4. waitwas continued for additional 1 hour
  5. customwas brought back to room temperature
  6. washwashed with water
  7. dry with materiala saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue thus obtained
  11. customwas purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-4a5ed146f509423cb0807849304716f4
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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